3,5-Bis(trifluoromethyl)benzoic acid → Methyl 3,5-bis(trifluoromethyl)benzoate

HRID 965818노트

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HRID 965818 반응식
[CH3:1][Si](C=[N+]=[N-])(C)C.[F:8][C:9]([F:24])([F:23])[C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1)[C:13]([OH:15])=[O:14]>C1(C)C=CC=CC=1.CO>[CH3:1][O:14][C:13](=[O:15])[C:12]1[CH:11]=[C:10]([C:9]([F:23])([F:24])[F:8])[CH:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:16]=1

참가 물질

5

반응물 2

HCID 128893,5-Bis(trifluoromethyl)benzoic acidHCID 167693Trimethylsilyldiazomethane

생성물 1

HCID 141265Methyl 3,5-bis(trifluoromethyl)benzoate

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매

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온도
0 °C

실험 절차

Trimethylsilyldiazomethane (11.5 mL) was added drop-wise to a solution of 3,5-bis-(trifluoromethyl)benzoic acid (2 g) in dry toluene (20 mL) and methanol (0.5 mL) previously cooled to 0° C. under a nitrogen atmosphere. The solution was stirred at r.t. for 1 hr, then concentrated in vacuo to give 3,5-bis-(trifluoromethyl)benzoic acid methyl ester (2 g) as a colourless oil. A solution of 3,5-bis-(trifluoromethyl)-benzoic acid methyl ester (2 g) and 1-vinyl-2-pyrrolidinone (863 μL) was added to a mixture of sodium hydride (60% suspension in mineral oil—0.41 g) in dry toluene (30 mL) previously heated to reflux. The mixture was stirred for 12 hrs, then it was partitioned between saturated ammonium chloride solution and AcOEt. The organic layer was dried, concentrated in vacuo and the residue was purified by flash chromatography (CH/AcOEt 8:2) to give the title compound (1.6 g) as a beige oil.

후처리

  1. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-52c32427ff8741889b5db36bc89d8727
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951861B1

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