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

HRID 626859ノート

反応式

HRID 626859 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-62ac302be5f645d0a66a677c3635c032
出典データセット
uspto-grants-2016_04
特許番号
US09309251B2

反応ノート

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