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

HRID 1592786ノート

反応式

HRID 1592786 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  1. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4e43ae70206a458592326b57ce5a99d0
出典データセット
uspto-grants-2007_11
特許番号
USRE039921E1

反応ノート

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