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

HRID 260421Notes

Reaction equation

HRID 260421 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8c5570ddf3ee4ec082c49fe9472d1e9a
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

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