Water → 3-Chloro-4-hydroxybenzyl alchol

HRID 82780ノート

反応式

HRID 82780 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[BH4-].[Na+].CCOC(C)=O.O>C1COCC1.CCO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[OH:10]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 170223-Chloro-4-hydroxybenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 2574563-Chloro-4-hydroxybenzyl alchol

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-chloro-4-hydroxybenzaldehyde (4.697 g, 30.0 mmol) and to trimethoxyborate (0.5 mL) in THF (20 mL) and EtOH (20 mL) was added NaBH4 (2.0 g, 52.87 mmol) in small portions over a period of 8 hours. The mixture was stirred overnight and EtOAc (100 mL) and water (50 mL) were added. The organic layer was separated and washed with 2M KHSO4 (30 mL) and brine (30 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography [SiO2, CHCl3/acetone (0.3:1)] followed by recrystallistion from EtOAc/hexane to give CAB06028 (3.82 g, 80%) as fine colorless needles: Mp. 126-127° C.; 1H NMR (400 MHz, DMSO-d6) δ 4.36 (d, J=6.5 Hz, 2H), 5.11 (t, J=6.5 Hz, 1H), 6.90 (d, J=8.2 Hz, 1H), 7.06 (dd, J=82, 2.0 Hz, 1H), 7.25 (d, J=2.0 Hz, 1H), 9.99 (s, 1H); 13C NMR (100.6 MHz, DMSO-d6) δ 62.1, 116.3, 119.2, 126.4, 128.1, 134.5, 151.7; LRMS (ES−): m/z 156.9 (100%, [M−H]).

後処理

  1. customThe organic layer was separated
  2. washwashed with 2M KHSO4 (30 mL) and brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography [SiO2, CHCl3/acetone (0.3:1)]
  6. customto give CAB06028 (3.82 g, 80%) as fine colorless needles

出典と根拠

ORDレコード
ord-1def485caa144645af27154cecfc98b8
出典データセット
uspto-grants-2014_09
特許番号
US08846737B2

反応ノート

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