Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate → HCID 18952387, compound

HRID 1492307

Reaction equation

HRID 1492307 reaction equation
[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH2:19][CH:20]=[CH2:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH2:19][CH2:20][CH3:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 19385705Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate

Product 1

HCID 18952387HCID 18952387, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate (14.4 g) (obtained as described in International patent application, publication no. WO 91/11999) in methanol (280 ml) was catalytically hydrogenated over 10% palladium on carbon (2.9 g) at 3 atmospheres pressure for 2 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:3 v/v), to give methyl 4-(t-butyldimethylsilyloxy)-3-propylbenzoate (B) (11.7 g) as an oil; NMR: 0.25(s, 6H), 0.95(t, 3H), 1.0(s, 9H), 1.5-1.7(m, 2H), 2.6(t, 2H), 3.9(s, 3H), 6.8(d, 1H), 7.8(dd, 1H), 7.8(s, 1H).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated by evaporation
  3. customThe residue was purified by flash chromatography
  4. washeluting with ethyl acetate/hexane (1:3 v/v)

Sources & evidence

ORD record
ord-86da75fd7f49456cb8a013750c1e6a8a
Source dataset
uspto-grants-1994_12
Patent number
US05373015

Linked notes

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