Hydrochloric Acid → 3-Phthalimido-4,4-difluoro-7-hydroxy-1-heptene

HRID 568985Notes

Reaction equation

HRID 568985 reaction equation
[C:1]1(=[O:22])[N:5]([CH:6]([C:9]([F:16])([F:15])[CH2:10][CH2:11][CH2:12][O:13]C)[CH:7]=[CH2:8])[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]12.C[Si](I)(C)C.Cl>ClCCl>[C:4]1(=[O:17])[N:5]([CH:6]([C:9]([F:15])([F:16])[CH2:10][CH2:11][CH2:12][OH:13])[CH:7]=[CH2:8])[C:1](=[O:22])[C:2]2=[CH:21][CH:20]=[CH:19][CH:18]=[C:3]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85247Trimethylsilyl iodideHCID 201495083-Phthalimido-4,4-difluoro-7-methoxy-1-heptene

Product 1

HCID 201494473-Phthalimido-4,4-difluoro-7-hydroxy-1-heptene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of nitrogen, a mixture of 3-phthalimido-4,4-difluoro-7-methoxy-1-heptene (440 mg, 1.43 mmoles) and trimethylsilyliodide (400 mg, 2 mmoles) in dry dichloromethane (10 ml) is heated overnight under reflux. 1N HCl (10 ml) is added to the reaction mixture which is kept under vigorous stirring for 1/2 hour. The organic layer is separated, washed successively with water, sodium bisulfite solution, and water, and is dried over sodium sulfate. 3-phthalimido-4,4-difluoro-7-hydroxy-1-heptene is obtained as a solid: 3.85 mg (91%).

Workup

  1. temperatureis heated overnight
  2. temperatureunder reflux
  3. customThe organic layer is separated
  4. washwashed successively with water, sodium bisulfite solution, and water
  5. dry with materialis dried over sodium sulfate

Sources & evidence

ORD record
ord-5f0a58f9b3764b3088227dd22569eaad
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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