Tetrahydrofuran → C6H5CH2Ocochfch3

HRID 2260849Notes

Reaction equation

HRID 2260849 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

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-eeb965ccad0b4b98b743f9b321011b5c
Source dataset
uspto-grants-1995_12
Patent number
US05478964

Reaction notes

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