Water → 5-Benzylthiomethyl-5-t-butyl-2,2-dimethyl-1,3-dioxane

HRID 704143Notes

Reaction equation

HRID 704143 reaction equation
[H-].[Na+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CS(O)(=O)=O.[C:16]([C:20]1([CH2:28]O)[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]1)([CH3:19])([CH3:18])[CH3:17].O>CN(C)C=O>[CH2:3]([S:10][CH2:28][C:20]1([C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:21][O:22][C:23]([CH3:27])([CH3:26])[O:24][CH2:25]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 867445215-t-Butyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane methanesulphonate

Product 1

HCID 200755965-Benzylthiomethyl-5-t-butyl-2,2-dimethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.25 g., 50% dispersion in oil) was added to a stirred solution of benzyl mercaptan (3.2 ml.) in dry dimethylformamide (75 ml) at 0°, under a current of nitrogen. Stirring was maintained for 30 minutes. 5-t-Butyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane methanesulphonate (7.5 g.) was added and the mixture was maintained at 130°, with stirring for 7 hours. The reaction mixture was cooled and poured into water. The aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and then evaporated in vacuo. 5-Benzylthiomethyl-5-t-butyl-2,2-dimethyl-1,3-dioxane (7.0 g.) was obtained as a mobile oil and was used without further purification.

Workup

  1. temperaturewas maintained for 30 minutes
  2. temperaturethe mixture was maintained at 130°
  3. stirringwith stirring for 7 hours
  4. temperatureThe reaction mixture was cooled
  5. extractionThe aqueous mixture was extracted with diethyl ether
  6. washThe ethereal extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-f16d892941394f6087be2e736bc3b0a9
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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