Ethyl ketone → 5-Fluoro-3-(3-hydroxypent-3-yl)[O-(3,4-dimethoxybenzyl)]phenol

HRID 260421

반응식

HRID 260421 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH:3]=1.[Li]CCCC.[CH3:26][CH2:27][C:28](=[O:31])[CH2:29][CH3:30]>C1COCC1>[F:8][C:6]1[CH:7]=[C:2]([C:28]([OH:31])([CH2:29][CH3:30])[CH2:27][CH3:26])[CH:3]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH:5]=1

참가 물질

5

반응물 3

HCID 7288Ethyl ketoneHCID 194269851-Bromo-3-(3,4-dimethoxybenzyloxy)-5-fluorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 701948305-Fluoro-3-(3-hydroxypent-3-yl)[O-(3,4-dimethoxybenzyl)]phenol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-bromo-3-(3,4-dimethoxybenzyloxy)-5-fluorobenzene (Step 1) (1.02 g) in THF (10 mL) at -78° C. was added n-BuLi (1.5 mL of a 2.2M solution) dropwise. After 30 min. 3-pentanone (0.33 mL) was added and after 30 min. the bath was removed and the mixture stirred for 10 min. The reaction mixture was quenched with NH4OAc buffer and extracted with EtOAc. The organics were dried (MgSO4) and concentrated. Chromatography of the residue (silica gel; hexane/EtOAc (3:1) provided the title compound as a colorless oil.

후처리

  1. customwas removed
  2. customThe reaction mixture was quenched with NH4OAc buffer
  3. extractionextracted with EtOAc
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8c5570ddf3ee4ec082c49fe9472d1e9a
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527827

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