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

HRID 626859Notes

Reaction equation

HRID 626859 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-62ac302be5f645d0a66a677c3635c032
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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