{3-[4-(t-Butyldimethylsilylhydroxy)but-1-ynyl]phenyl}acetic acid methyl ester → {3-[4-Hydroxybutyl]phenyl)acetic acid methyl ester

HRID 902622Notes

Reaction equation

HRID 902622 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[C:12][CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:6]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=1

Participants

5

Reactant 2

HCID 69253921{3-[4-(t-Butyldimethylsilylhydroxy)but-1-ynyl]phenyl}acetic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 59745064{3-[4-Hydroxybutyl]phenyl)acetic acid methyl esterYield 64.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of {3-[4-(t-butyidimethylsilyloxy)but-1-ynyl]phenyl}acetic acid methyl ester (700 mg, 2.1 mmol) in MeOH (15 ml) was treated with 5% Pd/C (100 mg) and hydrogen gas (1 atm) for 1 hr. The catalyst was filtered, and the solvent evaporated. The residue was dissolved in THF (1 ml), and treated with tetrabutyl ammonium fluoride (2 ml of a 1N solution in THF) for 2 hr. The reaction was diluted with water and extracted with diethyl ether. The organic extracts were washed with water, dried, evaporated, and the volatile organics removed by vacuum to give the title compound as an oil (300 mg, 64%). MS (ESI) 223.2 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in THF (1 ml)
  4. additiontreated with tetrabutyl ammonium fluoride (2 ml of a 1N solution in THF) for 2 hr
  5. additionThe reaction was diluted with water
  6. extractionextracted with diethyl ether
  7. washThe organic extracts were washed with water
  8. customdried
  9. customevaporated
  10. customthe volatile organics removed by vacuum

Sources & evidence

ORD record
ord-3e90e4209aa043d4a3e92a1e8dc2b895
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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