1-trifluoromethyl-1,2-benziodoxol-3(1H)-one → (R)-2-methyl-2-trifluoromethoxymethyl-but-3-enoic acid methyl ester

HRID 2176270

反応式

HRID 2176270 の反応式
[F:1][C:2]([F:14])([F:13])I1C2C=CC=CC=2C(=O)O1.[CH3:15][O:16][C:17](=[O:24])[C@:18]([CH2:22][OH:23])([CH3:21])[CH:19]=[CH2:20]>[2H]C(Cl)(Cl)Cl.ClCCl.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[Zn+2].[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>[CH3:15][O:16][C:17](=[O:24])[C@@:18]([CH3:21])([CH2:22][O:23][C:2]([F:14])([F:13])[F:1])[CH:19]=[CH2:20]

参加物

6

反応物 2

HCID 248509811-trifluoromethyl-1,2-benziodoxol-3(1H)-oneHCID 86706109HCID 86706109、化合物

生成物 1

HCID 86706114(R)-2-methyl-2-trifluoromethoxymethyl-but-3-enoic acid methyl ester収率 23.1%

試薬・触媒・溶媒 3

HCID 14940315168106-25-0触媒HCID 6344Dichloromethane溶媒HCID 71583Chloroform-D溶媒

実験手順

Zinc bis(trifluoromethylsulfonyl)imide (750 mg, 1.2 mmol) and (1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one (758 mg, 2.4 mmol) were added to a stirred solution of (R)-2-hydroxymethyl-2-methyl-but-3-enoic acid methyl ester (288 mg, 2.0 mmol) in dry deuterochloroform (4 mL) under nitrogen. The reaction mixture was stirred at room temperature under nitrogen in a sealed flask for 5 days. The resulting suspension was diluted with dichloromethane and the supernatant was separated and evaporated. Dichloromethane (5 mL) was added to the residue and the supernatant solution was purified by silica gel chromatography using a gradient of pentane/diethyl ether 10:1 to 5:1 to afford crude (R)-2-methyl-2-trifluoromethoxymethyl-but-3-enoic acid methyl ester (98 mg) as a clear oil which was used in the next step.

後処理

  1. customthe supernatant was separated
  2. customevaporated
  3. additionDichloromethane (5 mL) was added to the residue
  4. customthe supernatant solution was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-6fb46d62428f47cbafe6b18b691cc86d
出典データセット
uspto-grants-2015_06
特許番号
US09062092B2

関連ノート

読み込み中…