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

HRID 2167003Notes

Reaction equation

HRID 2167003 reaction equation
[H-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH:7]=[C:8]([Cl:10])[CH:9]=1.[CH3:17][C:18]1[CH:19]=[C:20]([C:29](=[O:31])[CH3:30])[S:21][C:22]=1[C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26].CC(OC)(C)C>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]([OH:16])([C:12]([F:13])([F:14])[F:15])[CH2:30][C:29]([C:20]2[S:21][C:22]([C:23]#[C:24][Si:25]([CH3:28])([CH3:26])[CH3:27])=[C:18]([CH3:17])[CH:19]=2)=[O:31])[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 62714Lithium hydrideHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 674301401-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone

Product 1

HCID 674291313-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-3-hydroxy-1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-butan-1-oneYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. additionthe reaction mixture is poured onto water (30 ml) at 5° C
  2. extractionThe organic phase is extracted with water
  3. dry with materiala saturated aqueous solution of NaCl, dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11d17de1a8d34b64a304c4651be80300
Source dataset
uspto-grants-2015_06
Patent number
US09044389B2

Reaction notes

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