Ozone → Ethyl 2-[4-chloro-3-fluoro-2-formyl-6-(2-methyl-1,3-dioxolan-2-yl)phenoxy]propanoate

HRID 626859노트

반응식

HRID 626859 반응식
[Cl:1][C:2]1[CH:15]=[C:14]([C:16]2([CH3:21])[O:20][CH2:19][CH2:18][O:17]2)[C:5]([O:6][CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH:22]=C)[C:3]=1[F:24].[O:25]=[O+][O-]>C(Cl)Cl>[Cl:1][C:2]1[CH:15]=[C:14]([C:16]2([CH3:21])[O:20][CH2:19][CH2:18][O:17]2)[C:5]([O:6][CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH:22]=[O:25])[C:3]=1[F:24]

참가 물질

4

반응물 2

HCID 24823OzoneHCID 86697550Ethyl 2-[4-chloro-3-fluoro-6-(2-methyl-1,3-dioxolan-2-yl)-2-vinylphenoxy]propanoate

생성물 1

HCID 86697551Ethyl 2-[4-chloro-3-fluoro-2-formyl-6-(2-methyl-1,3-dioxolan-2-yl)phenoxy]propanoate수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of ethyl 2-[4-chloro-3-fluoro-6-(2-methyl-1,3-dioxolan-2-yl)-2-vinylphenoxy]propanoate (400 mg, 1.11 mmol) in methylene chloride (40 mL) at −78° C. was treated with ozone until a purple color persisted. The reaction mixture was purged with oxygen, treated with dimethyl sulfide (1 mL) and warmed to room temperature. The reaction mixture was concentrated to give the crude product (392 mg, 98%) as a mixture of enantiomers that was used without further purification. LCMS calculated for C16H19ClFO6 (M+H)+: m/z=361.1; found: 361.1.

후처리

  1. customThe reaction mixture was purged with oxygen
  2. additiontreated with dimethyl sulfide (1 mL)
  3. concentrationThe reaction mixture was concentrated

출처 및 근거

ORD 기록
ord-62ac302be5f645d0a66a677c3635c032
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309251B2

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