Water → Methyl(E)-8-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-6-oxo-7-octenoate

HRID 2243292Notes

Reaction equation

HRID 2243292 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])(OCC)=O)C.[Si:22]([O:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=O)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>C1COCC1>[Si:22]([O:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1/[CH:32]=[CH:11]/[C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10900635Benzaldehyde, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-HCID 15546840Methyl 7-(diethoxyphosphoryl)-6-oxoheptanoate

Product 1

HCID 23118874Methyl(E)-8-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-6-oxo-7-octenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon, 0.26 g (10.87 mmol) of sodium hydride was added to a solution of 3.20 g (10.87 mmol) of methyl 7-(diethoxyphosphoryl)-6-oxoheptanoate from Ex. XIIb in 53 ml of THF. The mixture was stirred at room temperature for 30 min, a solution of 9.06 mmol of 2-{[tert-butyl(dimethyl)silyl]oxy}benzaldehyde from Ex. XIIa in 20 ml of THF was added and the mixture was stirred at room temperature for 18 h. Water was added, the mixture was extracted with ethyl acetate, the combined organic phases were dried over Na2SO4 and the solvent was removed. The product was purified chromatographically (silica gel, cyclohexane/EA 10:1). This gave 2.51 g (67.8%) of a colorless liquid.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. customthe solvent was removed
  5. customThe product was purified chromatographically (silica gel, cyclohexane/EA 10:1)

Sources & evidence

ORD record
ord-0f6a3a0ad00d462191566b2cd05e80cd
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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