Water → 5-Acetylthiomethyl-5-ethyl-2,2-dimethyl-1,3-dioxane

HRID 704130Notes

Reaction equation

HRID 704130 reaction equation
[H-].[Na+].[S:3]1C=C[CH:5]=[C:4]1CC(O)=O.[CH3:12][C:13]1([CH3:23])[O:18][CH2:17][C:16]([CH2:21][CH3:22])([CH2:19]I)[CH2:15][O:14]1.[OH2:24]>CN(C)C=O>[C:4]([S:3][CH2:19][C:16]1([CH2:21][CH3:22])[CH2:17][O:18][C:13]([CH3:23])([CH3:12])[O:14][CH2:15]1)(=[O:24])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 159702-Thiopheneacetic acidHCID 24758Sodium hydrideHCID 200756052,2-Dimethyl-5-ethyl-5-iodomethyl-1,3-dioxane

Product 1

HCID 200755985-Acetylthiomethyl-5-ethyl-2,2-dimethyl-1,3-dioxane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (340 mg., 50% dispersion in paraffin oil) was added carefully to a stirred solution of thiolacetic acid (500 mg.) in dry dimethylformamide (100 ml.) at 20°. After 30 minutes 2,2-dimethyl-5-ethyl-5-iodomethyl-1,3-dioxane (2.0 g.) was added. The mixture was refluxed with stirring for 2 hours. The mixture was cooled and poured into water. The aqueous mixture was extracted with ether. The ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. The solution was evaporated in vacuo. The residue was purified by column chromatography on silica, eluting with 1:4 ether:hexane. 5-Acetylthiomethyl-5-ethyl-2,2-dimethyl-1,3-dioxane was obtained as a pale yellow oil (1.5 g.)

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureThe mixture was cooled
  3. extractionThe aqueous mixture was extracted with ether
  4. washThe ethereal extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customThe solution was evaporated in vacuo
  7. customThe residue was purified by column chromatography on silica
  8. washeluting with 1:4 ether

Sources & evidence

ORD record
ord-b6628ac91d4d4803833f2c5de59fe6a8
Source dataset
uspto-grants-1991_01
Patent number
US04985582

Reaction notes

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