Water → Diethyl 2-fluoro-2-phenylmalonate

HRID 2260847Notes

Reaction equation

HRID 2260847 reaction equation
[C:1]1([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[K+].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:30])(=O)=O)=CC=1.O>CCOCC>[C:1]1([C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[F:30])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 66514Diethyl phenylmalonateHCID 82127Potassium hydrideHCID 588007N-Fluorobenzenesulfonimide

Product 1

HCID 4246642Diethyl 2-fluoro-2-phenylmalonateYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-20 °C

Procedure

1 millimole of diethyl phenylmalonate was stirred with potassium hydride in 2 milliliters ether for 30 minutes at -25° C. 1.2 molar equivalents N-fluorobenzenesulfonimide prepared according to Example 1 above in 2 milliliters ether were dropped into the mixture which was stirred for 1 hour at -20° C. The mixture was allowed to warm up to room temperature and water was added. The product was extracted into ether which was dried and evaporated. Purification was carried out on a silica gel column. C6H5CF(COOCH2CH3)2 was obtained in 47% yield.

Workup

  1. additionwere dropped into the mixture which
  2. temperatureto warm up to room temperature
  3. extractionThe product was extracted into ether which
  4. customwas dried
  5. customevaporated
  6. customPurification

Sources & evidence

ORD record
ord-b1f1903fc6e6458087132419d90e0eb2
Source dataset
uspto-grants-1995_12
Patent number
US05478964

Reaction notes

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