Methyl (trimethylsilyl)acetate → (E)-Methyl 2-(6-(benzyloxy)-2,2-dimethyl-2,3-dihydroinden-1-ylidene)acetate

HRID 2098965Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si](C)(C)[CH2:13][C:14]([O:16][CH3:17])=[O:15].[CH2:20]([O:27][C:28]1[CH:36]=[C:35]2[C:31]([CH2:32][C:33]([CH3:39])([CH3:38])[C:34]2=O)=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.CCOC(C)=O>[CH2:20]([O:27][C:28]1[CH:36]=[C:35]2[C:31]([CH2:32][C:33]([CH3:39])([CH3:38])/[C:34]/2=[CH:13]\[C:14]([O:16][CH3:17])=[O:15])=[CH:30][CH:29]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: -78 °C

Procedure

At −78° C., lithium bis(trimethylsilyl)amide (1.0 M in THF) (3.6 mL, 3.6 mmol) was added slowly to a solution of methyl 2-(trimethylsilyl)acetate (0.59 mL, 3.6 mmol) in THF (20 mL). The mixture was maintained at −78° C. for 7 minutes and then 6-(benzyloxy)-2,2-dimethyl-2,3-dihydroinden-1-one (8.3) (0.535 g, 2.0 mmol) was added in one portion. The resulting mixture was stirred at −78° C. and allowed to warm to room temperature overnight. The reaction mixture was then diluted with EtOAc (200 mL), washed with water and brine, and dried over anhydrous sodium sulfate. After removing solvent, the residue was purified by chromatography (silica gel, 1:5 EtOAc/hexane) to give product 8.4 in 45% yield.

Workup

temperatureto warm to room temperature overnight
washwashed with water and brine
dry with materialdried over anhydrous sodium sulfate
customAfter removing solvent
customthe residue was purified by chromatography (silica gel, 1:5 EtOAc/hexane)

Sources & evidence

ORD record: ord-49a907eaa4cc4f1ea9d5b4248f92bb8d
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450522B2

Reaction notes

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