Water → 3-Chloro-4-hydroxybenzyl alchol

HRID 82780노트

반응식

HRID 82780 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 2574563-Chloro-4-hydroxybenzyl alchol

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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]).

후처리

  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

출처 및 근거

ORD 기록
ord-1def485caa144645af27154cecfc98b8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846737B2

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