Ethyl Acetate → (E)-Methyl 2-(5-(benzyloxy)cyclobutabenzen-1(2H)-ylidene)acetate

HRID 2098960Notes

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:29]=[CH:30][C:31]2[CH2:35][C:34](=O)[C:32]=2[CH:33]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCOC(C)=O>C1COCC1>[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]2[CH2:35]/[C:34](=[CH:13]\[C:14]([O:16][CH3:17])=[O:15])/[C:32]=2[CH:33]=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) (7.1 mL, 7.1 mmol) was added slowly to a solution of methyl 2-(trimethylsilyl)acetate (1.2 mL, 7.1 mmol) in THF (6 mL). It was maintained at −78° C. for 12 min. 5-(Benzyloxy)cyclobutabenzen-1(2H)-one (3.2) (0.88 g, 3.9 mmol) in THF (3 mL) was added in one portion. It was stirred at −78° C. and allowed to r.t. overnight. EtOAc (300 mL) was added and it was washed with brine and dried over Na2SO4. After removing solvent, the residue was purified by chromatography (silica gel, 1:6 EtOAc/hexane) to give 3.4 in 14% yield.

Workup

washit was washed with brine
dry with materialdried over Na2SO4
customAfter removing solvent
customthe residue was purified by chromatography (silica gel, 1:6 EtOAc/hexane)
customto give 3.4 in 14% yield

Sources & evidence

ORD record: ord-8100bdd44bdb4e1c92e9fcc5e47d6583
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450522B2

Reaction notes

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