Methyl 3-(3-(tert-butyldimethylsilyloxy)-2,5-difluorophenyl)pent-2-enoate → Methyl 3-(3-(tert-butyldimethylsilyloxy)-2,5-difluorophenyl)pentanoate

HRID 1662565Notes

Reaction equation

HRID 1662565 reaction equation
[Si:1]([O:8][C:9]1[C:10]([F:24])=[C:11]([C:16]([CH2:22][CH3:23])=[CH:17][C:18]([O:20][CH3:21])=[O:19])[CH:12]=[C:13]([F:15])[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[Pd].CO>[Si:1]([O:8][C:9]1[C:10]([F:24])=[C:11]([CH:16]([CH2:22][CH3:23])[CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:12]=[C:13]([F:15])[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67432312Methyl 3-(3-(tert-butyldimethylsilyloxy)-2,5-difluorophenyl)pent-2-enoate

Product 1

HCID 57706858Methyl 3-(3-(tert-butyldimethylsilyloxy)-2,5-difluorophenyl)pentanoateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 75 mL pressure tube was charged with 90.E (mixture of geometric isomers) (0.26 g, 0.73 mmol), MeOH (7 mL), and Pd/C (10 wt. %) (0.039 g, 0.036 mmol). The tube was purged 3 times with H2 at 50 psi and sealed. The mixture was stirred for 8 hours at room temperature, filtered through silica gel (EtOAc), and concentrated to afford 90.F (0.23 g, 88% yield) as a colorless oil. The product thus obtained was used without further purification.

Workup

  1. customThe tube was purged 3 times with H2 at 50 psi
  2. customsealed
  3. filtrationfiltered through silica gel (EtOAc)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d4a1e7304bce4ec7867d148bf94dc52e
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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