Water → HCID 20063409, compound

HRID 1084349Notes

Reaction equation

HRID 1084349 reaction equation
[F:1][C:2](=[CH:5][CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH:3]=[O:4].[Na].C1(S)C=CC=CC=1.O>CCCCCC>[F:1]/[C:2](=[CH:5]\[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:11])/[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 5360545SodiumHCID 54231229HCID 54231229, compound

Product 1

HCID 20063409HCID 20063409, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

5.50 Grams of 2-fluoro-5-(tert-butyldimethylsilyloxy)-2-pentenal (E form:Z form=11:1) was dissolved in 50 ml of dry hexane, and after adding 20 mg of the sodium salt of thiophenol, the resulting solution was heated under reflux for 20 hours with stirring. Thereafter, 10 ml of water was added to the reaction solution, and the toluene layer was separated. The aqueous layer was extracted twice with ether, and the ether extracts were combined with the above toluene layer. This mixture was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 5.50 g of (Z)-2-fluoro-5-(tert-butyldimethylsilyloxy)-2-pentenal.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 20 hours
  3. customthe toluene layer was separated
  4. extractionThe aqueous layer was extracted twice with ether
  5. washThis mixture was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c24c7f74d8034aeaade0e4fc6bf64c23
Source dataset
uspto-grants-1991_04
Patent number
US05004753

Reaction notes

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