(S)-4-Fluoro-3-phenoxybenzaldehyde-cyanhydrine → (S)alpha-cyano-3-phenoxy-4-fluoro-benzyl (1R,cis,E) 2,2-dimethyl-3-[2-fluoro-3-oxo-3-(1,1-dimethyl-ethoxy)-1-propenyl]-cyclopropanecarboxylate

HRID 1383210Notes

Reaction equation

HRID 1383210 reaction equation
[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[C:6](/[F:14])\[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C@H:3]1[C:15]([OH:17])=[O:16].[C:19]([C@@H:21](O)[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:23]=1)#[N:20]>>[CH3:1][C:2]1([CH3:18])[C@@H:4](/[CH:5]=[C:6](/[F:14])\[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C@H:3]1[C:15]([O:17][C@H:21]([C:19]#[N:20])[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:23]=1)=[O:16]

Participants

3

Reactant 2

HCID 12803645(S)-4-Fluoro-3-phenoxybenzaldehyde-cyanhydrineHCID 13372597(1R,cis,E) 2,2-dimethyl-3-[2-fluoro-3-oxo-3-(1,1-dimethyl-ethoxy)-1-propenyl]-cyclopropane carboxylic acid

Product 1

HCID 13372614(S)alpha-cyano-3-phenoxy-4-fluoro-benzyl (1R,cis,E) 2,2-dimethyl-3-[2-fluoro-3-oxo-3-(1,1-dimethyl-ethoxy)-1-propenyl]-cyclopropanecarboxylate

Procedure

Using the procedure of Step B of Example 43, (1R,cis,E) 2,2-dimethyl-3-[2-fluoro-3-oxo-3-(1,1-dimethyl-ethoxy)-1-propenyl]-cyclopropane carboxylic acid and (S)α-cyano-3-phenoxy-4-fluoro-benzyl alcohol were reacted to obtain (S)α-cyano-3-phenoxy-4-fluoro-benzyl (1R,cis,E) 2,2-dimethyl-3-[2-fluoro-3-oxo-3-(1,1-dimethyl-ethoxy)-1-propenyl]-cyclopropanecarboxylate melting at 122° and having a specific rotation of [α]D20 =+61°±2.5° (c=0.35% in chloroform).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-42c1eafef2c344438e262ad72fbcf5eb
Source dataset
uspto-grants-1989_02
Patent number
US04808749

Reaction notes

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