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

HRID 2176270

반응식

HRID 2176270 반응식
[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]

참가 물질

6

반응물 2

HCID 248509811-trifluoromethyl-1,2-benziodoxol-3(1H)-oneHCID 86706109HCID 86706109, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 14940315168106-25-0촉매HCID 6344Dichloromethane용매HCID 71583Chloroform-D용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6fb46d62428f47cbafe6b18b691cc86d
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062092B2

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