3-Bromo-2,5-dimethoxybenzaldehyde → 3-Bromo-2,5-dimethoxybenzyl Alcohol

HRID 1835994

반응식

HRID 1835994 반응식
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

참가 물질

4

반응물 2

HCID 9310963-Bromo-2,5-dimethoxybenzaldehydeHCID 21226445Aluminium lithium hydride

생성물 1

HCID 101927773-Bromo-2,5-dimethoxybenzyl Alcohol수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cooled (0° C.) solution of 51 (8.0 g, 33 mmol) in THF (100 ml) was added LiAlH4 (15 ml of 1.0M in THF) dropwise. After 15 min, the reaction was quenched with 2N HCl and the aqueous layer was extracted with EtOAc. The EtOAc layer was dried concentrated to give a solid (7.5 g, 93%): Mp=65-67° C.; 1H NMR (DMSO-d6) δ 7.05 (d, 1 H, J=3.0 Hz), 6.98 (d, 1 H, J=2.5 Hz), 5.28 (t, 1 H, J=4.9 Hz), 4.47 (d, 2 H, J=5.7 Hz), 3.73 (s, 3 H), 3.67 (s, 3 H); MS 245 (M−H)−

후처리

  1. customthe reaction was quenched with 2N HCl
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe EtOAc layer was dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f03923f1153f4479855097c93705d95a
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774248B2

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