2-Fluoroethanol → benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-(2-fluoroethoxy)-1-propenyl]cyclopropane-carboxylate

HRID 1719772Notes

Reaction equation

HRID 1719772 reaction equation
[F:1][CH2:2][CH2:3][OH:4].[CH3:5][C:6]1([CH3:28])[C@@H:8](/[CH:9]=[CH:10]\[C:11](=O)[O:12]C(C)(C)C)[C@H:7]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>C(Cl)(Cl)Cl>[CH3:5][C:6]1([CH3:28])[C@@H:8](/[CH:9]=[CH:10]\[C:11](=[O:12])[O:4][CH2:3][CH2:2][F:1])[C@H:7]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Participants

4

Reactant 2

HCID 97372-FluoroethanolHCID 86740330benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-tert.-butoxy-1-propenyl]-cyclopropane-carboxylate

Product 1

HCID 13335682benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-(2-fluoroethoxy)-1-propenyl]cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 48, 2-fluoro-ethanol and the product of Step A were reacted to obtain benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-(2-fluoroethoxy)-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+53° (c=0.5% in chloroform).

Sources & evidence

ORD record
ord-28fc30063de64d0fb4c20093493d6ccf
Source dataset
uspto-grants-1985_09
Patent number
US04542142

Reaction notes

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