Water → HCID 14837915, compound

HRID 986335Notes

Reaction equation

HRID 986335 reaction equation
[OH:1][C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][C:5](=[O:7])[CH:4]=[CH:3]1.FC(F)(F)S(O[Si:25]([CH3:28])([CH3:27])[CH3:26])(=O)=O.O.CCOCC>C(N(C(C)C)CC)(C)C>[O:12]([CH2:11][CH2:10][CH2:9][CH2:8][C:2]1([O:1][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:6][C:5](=[O:7])[CH:4]=[CH:3]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 65367Trimethylsilyl triflateHCID 20158426HCID 20158426, compound

Product 1

HCID 14837915HCID 14837915, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 1.2 g (4.9 mmoles) of 4-hydroxy-4-(4-phenoxybutyl)-2-cyclopentenone in 10 ml of diisopropylethylamine was cooled to 0° C. in an atmosphere of nitrogen, and 20 ml (10 mmoles) of trimethylsilyl trifluoromethanesulfonate (5 M dichloromethane solution) was added. The mixture was stirred for 20 minutes. After the reaction, water was added, and the mixture was exracted with ether. The extract was washed with water and an aqueous sodium chloride solution, and then dried. The solvent was distilled off under reduced pressure. The residue was chromatographed on a silica gel column (n-hexane:AcOEt=10:1) to give 1.2 g (77%) of 4-(4-phenoxybutyl)-4-trimethylsilyloxy-2-cyclopentenone.

Workup

  1. additionwas added
  2. additionwas added
  3. washThe extract was washed with water
  4. dry with materialan aqueous sodium chloride solution, and then dried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was chromatographed on a silica gel column (n-hexane:AcOEt=10:1)

Sources & evidence

ORD record
ord-0c52ef9beeae4eb1a46004361250a01a
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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