Tetrahydrofuran → C6H5CH2Ocochfch3

HRID 1656809Notes

Reaction equation

HRID 1656809 reaction equation
CC1(F)CC[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:24])(=O)=O)=CC=1.[O:34]1C[CH2:37][CH2:36][CH2:35]1>>[C:4]1([CH2:3][O:12][C:35]([CH:36]([CH3:37])[F:24])=[O:34])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 588007N-FluorobenzenesulfonimideHCID 150144562-Fluoro-2-methyl-1-tetralone

Product 1

HCID 15014458C6H5CH2Ocochfch3Yield 47%

Procedure

This Example is directed to the fluorination of ethyl phenylacetate (C6H5CH2CO2C2H5) to form C6H5CH2CO2CHFCH3. The precursor was stirred with 2 millimoles lithium diisopropylamine (preparation described in Example 12) in tetrahydrofuran at -78° C. for 1 hour. 1.2 equivalents N-fluorobenzenesulfonimide prepared according to Example 1 above in 3 milliliters tetrahydrofuran were added to the mixture which was stirred for 80 minutes. Stirring was continued as the mixture was allowed to warm up to room temperature, quenched with ammonium chloride, extracted with dichloromethane, dried, and evaporated. Purification was carried out on a silica gel column. C6H5CH2OCOCHFCH3 was obtained in 47% yield.

Workup

  1. additionwere added to the mixture which
  2. stirringStirring
  3. customquenched with ammonium chloride
  4. extractionextracted with dichloromethane
  5. customdried
  6. customevaporated
  7. customPurification

Sources & evidence

ORD record
ord-8e03683f9d2a4a5b9f8cf7122e214b18
Source dataset
uspto-grants-1993_10
Patent number
US05254732

Reaction notes

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