Water → HCID 89975748, compound

HRID 716164Notes

Reaction equation

HRID 716164 reaction equation
[SH2:1].[Na].Cl[CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH:7]=[O:8].C(OCC)(=O)C.O>CN(C)C=O>[C:9]1([CH:4]2[S:1][CH:7]([OH:8])[CH2:6][CH2:5]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 56989771HCID 56989771, compoundHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 89975748HCID 89975748, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

32 mg of anhydrous sodium hydrogen sulfide was added to a solution of 61 mg of 4-chloro-4-phenylbutanal in 1 mL of N,N-dimethylformamide at a temperature of 0° C. to 10° ° C. and the obtained mixture was then stirred at the same temperature as described above for 1 hour. Thereafter, ethyl acetate and water were added to the reaction mixture, and the water layer was then removed. The organic layer was washed with water, and was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=85/15 to 60/40), so as to obtain 37 mg of 5-phenylthiolan-2-ol in the form of a colorless oily product.

Workup

  1. customas described above for 1 hour
  2. customthe water layer was then removed
  3. washThe organic layer was washed with water
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. distillationAfter that, the solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=85/15 to 60/40)

Sources & evidence

ORD record
ord-bc0d55588c0f44d5a2e9ad666f368f71
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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