2-methyl-1-benzofuran-6-ol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This material was prepared from 6-hydroxy-2-methylbenzofuran (654 mg, 4.41 mmole) by treatment with acetyl chloride (0.41 ml, 5.74 mmole) and triethylamine (0.74 ml, 5.30 mmole) in a manner as previously described for 8b to give the desired product as an oil (850 mg, ˜quant). 1H NMR (CDCl3) δ7.41 (1H, d, J=8.3 Hz), 7.13 (1H, s), 6.88 (1H, dd, J=8.3, 1.9 Hz), 6.32 (1H, s), 2.42 (3H, s), 2.30 (3H, s).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This material was prepared from 6-methoxy-2-methylbenzofuran (1.00 g, 6.17 mmole) by treatment with BBr3 in a manner as previously described for 1d to give a colorless oil (690 mg, 75%) which solidified on standing. 1H NMR (DMSO-d6) δ9.32 (1H, s), 7.23 (1H, d, J=8.3 Hz), 6.80 (1H, s), 6.64 (1H, d, J=8.3 Hz), 6.37 (1H, s), 2.35 (3H, s).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This material was prepared from 6-methoxy-2-methylbenzofuran (1.00 g, 6.17 mmole) by treatment with BBr3 in a manner as previously described for 1d to give a colorless oil (690 mg, 75%) which solidified on standing. 1H NMR (DMSO-d6) δ9.32 (1H, s), 7.23 (1H, d, J=8.3 Hz), 6.80 (1H, s), 6.64 (1H, d, J=8.3 Hz), 6.37 (1H, s), 2.35 (3H, s).

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 6-Methoxy-2-methyl-benzofuran 125-A (1.76 g, 10.85mmol) in 45 ml of CH2Cl2 at −5° C. was added BBr3 (24 ml of 1M BBr3 in CH2Cl2, 16 28 mmol). The reaction was allowed to warm to 0° C. and stirred at that temperature for 1.5 hr. The reaction was poured into a mixture of ice and saturated aqueous NaHCO3 and layers were separated. The aqueous layer was re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to a brown oil. The residue was chromatographed on silica gel eluting CH2Cl2 to give 872 mg (54%) of 6-Hydroxy-2-methyl-benzofuran 125-B. were separated The aqueous layer was re-extracted with CH2Cl2 The combined organic layers were dried (MgSO4) concentrated under reduced pressure to a brown oil The residue was chromatographed on silica gel eluting CH2Cl2

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 6-Methoxy-2-methyl-benzofuran 125-A (1.76 g, 10.85mmol) in 45 ml of CH2Cl2 at −5° C. was added BBr3 (24 ml of 1M BBr3 in CH2Cl2, 16 28 mmol). The reaction was allowed to warm to 0° C. and stirred at that temperature for 1.5 hr. The reaction was poured into a mixture of ice and saturated aqueous NaHCO3 and layers were separated. The aqueous layer was re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to a brown oil. The residue was chromatographed on silica gel eluting CH2Cl2 to give 872 mg (54%) of 6-Hydroxy-2-methyl-benzofuran 125-B. were separated The aqueous layer was re-extracted with CH2Cl2 The combined organic layers were dried (MgSO4) concentrated under reduced pressure to a brown oil The residue was chromatographed on silica gel eluting CH2Cl2

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 6-Methoxy-2-methyl-benzofuran 125-A (1.76 g, 10.85 mmol) in 45 ml of CH2Cl2 at −5° C. was added BBr3 (24 ml of 1M BBr3 in CH2Cl2, 16.28 mmol). The reaction was allowed to warm to 0° C. and stirred at that temperature for 1.5 hr. The reaction was poured into a mixture of ice and saturated aqueous NaHCO3 and layers were separated. The aqueous layer was re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to a brown oil. The residue was chromatographed on silica gel eluting CH2Cl2 to give 872 mg (54%) of 6-Hydroxy-2-methyl-benzofuran 125-B. Anal calc'd for C9H8O2: C, 72.96; H, 5.44. Found: C, 72.72; H, 5.43. were separated The aqueous layer was re-extracted with CH2Cl2 The combined organic layers were dried (MgSO4) concentrated under reduced pressure to a brown oil The residue was chromatographed on silica gel eluting CH2Cl2

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This material was prepared from 6-hydroxy-2-methylbenzofuran (654 mg, 4.41 mmole) by treatment with acetyl chloride (0.41 ml, 5.74 mmole) and triethylamine (0.74 ml, 5.30 mmole) in a manner as previously described for 8b to give the desired product as an oil (850 mg, ˜quant). 1H NMR (CDCl3) δ 7.41 (1H, d, J=8.3 Hz), 7.13 (1H, s), 6.88 (1H, dd, J=8.3, 1.9 Hz), 6.32 (1H, s), 2.42 (3H, s), 2.30 (3H, s).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This material was prepared from 6-methoxy-2-methylbenzofuran (1.00 g, 6.17 mmole) by treatment with BBr3 in a manner as previously described for 1d to give a colorless oil (690 mg, 75%) which solidified on standing. 1H NMR (DMSO-d6) δ 9.32 (1H, s), 7.23 (1H, d, J=8.3 Hz), 6.80 (1H, s),6.64 (1H, d, J=8.3 Hz), 6.37 (1H, s), 2.35 (3H, s).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This material was prepared from 6-hydroxy-2-methylbenzofuran (654 mg, 4.41 mmole) by treatment with acetyl chloride (0.41 ml, 5.74 mmole) and triethylamine (0.74 ml, 5.30 mmole) in a manner as previously described for 8b to give the desired product as an oil (850 mg, ˜quant). 1H NMR (CDCl3) δ7.41 (1H, d, J=8.3 Hz), 7.13 (1H, s), 6.88 (1H, dd, J=8.3, 1.9 Hz), 6.32 (1H, s), 2.42 (3H, s), 2.30 (3H, s).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This material was prepared from 6-methoxy-2-methylbenzofuran (1.00 g, 6.17 mmole) by treatment with BBr3 in a manner as previously described for 1d to give a colorless oil (690 mg, 75%) which solidified on standing. 1H NMR (DMSO-d6) δ9.32 (1H, s), 7.23 (1H, d, J=8.3 Hz), 6.80 (1H, s), 6.64 (1H, d, J=8.3 Hz), 6.37 (1H, s), 2.35 (3H, s).