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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 390770Generated: October 29, 2026

tert-Butyl methyl ether → 3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-butan-1-one

https://huagongshe.com/reaction/390770

Reaction equation

Participants

RoleNameHCIDCharge
Reactanttert-Butyl methyl etherHCID 15413—
ReactantLithium hydrideHCID 62714—
Reactant1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 2758231—
Reactant1-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanoneHCID 67430140—
SolventTetrahydrofuranHCID 8028—
Product3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-butan-1-oneHCID 6742913156.1%

Reaction Steps

LiH (1.72 g) is added to a solution of 3′,5′-dichloro-2,2,2-trifluoroacetophenone (26.6 g) and 1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone (18.2 g) in THF (100 ml). After 30 minutes at 60° C. MTBE is added (200 ml) and the reaction mixture is poured onto water (30 ml) at 5° C. The organic phase is extracted with water and a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield 3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-butan-1-one (20.7 g). The crude product is used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08383659B2
Source datasetuspto-grants-2013_02
ORD IDord-d66b41011a8a4fc48eeafc8bfa0112b9
Source noteuspto-grants-2013_02