Methanol → 6-Hydroxy-2,3-dihydro-1H-isoindol-1-one

HRID 1761023ノート

反応式

HRID 1761023 の反応式
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][NH:8][C:9]2=[O:12])=[CH:5][CH:4]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][NH:8][C:9]2=[O:12])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 887MethanolHCID 25134Boron tribromideHCID 140056236-Methoxy-2,3-dihydro-1H-isoindol-1-one

生成物 1

HCID 115283646-Hydroxy-2,3-dihydro-1H-isoindol-1-one収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 6-methoxy-2,3-dihydro-isoindol-1-one (167 mg, 1.0 mmol) and boron tribromide (1 M in CH2Cl2, 3.6 mL, 3.6 mmol) in CH2Cl2 (8 mL) at −78° C. was stirred for 18 h at RT. The mixture was then cooled to −78° C. and MeOH (20 mL) was added. After 2 h at −78° C. the mixture was evaporated and the residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 9:1) to afford the title product (147 mg, 100%) as a white solid. MS m/e=148.0 (M−H+).

後処理

  1. temperatureThe mixture was then cooled to −78° C.
  2. customAfter 2 h at −78° C. the mixture was evaporated
  3. customthe residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 9:1)

出典と根拠

ORDレコード
ord-530ca7994aa4463cb7b34054dda6e966
出典データセット
uspto-grants-2005_01
特許番号
US06846832B2

反応ノート

読み込み中…