Ethyl trimethylsilylacetate → [1-[5-(4-Fluorobenzyl)furan-2-yl]vinyloxy]-trimethylsilane

HRID 11239Notes

Reaction equation

HRID 11239 reaction equation
[C:1]([C:4]1[O:5][C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:7][CH:8]=1)(=[O:3])[CH3:2].C(OC(=O)[CH2:21][Si:22](C)([CH3:24])[CH3:23])C>C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][C:6]2[O:5][C:4]([C:1]([O:3][Si:22]([CH3:24])([CH3:23])[CH3:21])=[CH2:2])=[CH:8][CH:7]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 77687Ethyl trimethylsilylacetateHCID 101306401-[5-[(4-Fluorophenyl)methyl]-2-furanyl]ethanone

Product 1

HCID 21972883[1-[5-(4-Fluorobenzyl)furan-2-yl]vinyloxy]-trimethylsilaneYield 88%

Reagents, catalysts & solvents 2

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-acetyl-5-(4-fluorobenzyl)furan (10 g, 46 mmol) and trimethylsilylacetic acid ethyl ester (10.9 g, 68 mmol) in anhydrous THF (30 ml) was cooled at −20° C. To a solution was added anhydrous tetrabutylammoniumfluoride (0.2 g). The reaction mixture was gradually warmed up to room temperature and stirred for 15 minutes at 50° C. The THF was evaporated under reduced pressure. The residue was distilled under reduced pressure. The fraction showing b.p. 130° C. (0.5 mmHg) was collected to give [1-[5-(4-fluorobenzyl)furan-2-yl]vinyloxy]-trimethylsilane (11.7 g). Yield 88%.

Workup

  1. customThe THF was evaporated under reduced pressure
  2. distillationThe residue was distilled under reduced pressure
  3. customwas collected

Sources & evidence

ORD record
ord-719ecd62b0b94a0fbbe448ddbdc6e91c
Source dataset
uspto-grants-2006_08
Patent number
US07098201B2

Reaction notes

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