Water → HCID 10374796, compound

HRID 257207Notes

Reaction equation

HRID 257207 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:14])[O:9][C:8]2[CH:10]=[CH:11][S:12][C:7]=2[C:6](=O)[CH2:5]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:3][C:4]1([CH3:14])[O:9][C:8]2[CH:10]=[CH:11][S:12][C:7]=2[CH:6]=[CH:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 15643884129969-30-8

Product 1

HCID 10374796HCID 10374796, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (3.27 g, 86.3 mmol) was added to a solution of 5,6-dihydro-5,5-dimethyl-7H-thieno [3,2-b]-pyran-7-one (12.1 g, 66.4 mmol) in ethanol (100 mL) and the resultant mixture was stirred at rt for 17 h. The mixture was poured into water (400 mL) and extracted with dichloromethane (2×100 mL). The dichloromethane solution was washed with water (5×), dried over sodium sulfate, and filtered. Molecular sieves (12 g) and p-toluenesulfonic acid (1.2 g, 6.3 mmol) was added to the resultant solution and stirred at 0° C. for 1.5 h. The reaction mixture was filtered, washed with saturated aqueous sodium bicarbonate and dried over sodium sulfate. The solvent was evaporated in vacuo to give the product, 11.0 g (99%), as a red oil which was identical in all respects to the product described in Method A.

Workup

  1. extractionextracted with dichloromethane (2×100 mL)
  2. washThe dichloromethane solution was washed with water (5×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. filtrationThe reaction mixture was filtered
  6. washwashed with saturated aqueous sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated in vacuo
  9. customto give the product, 11.0 g (99%)

Sources & evidence

ORD record
ord-4aaefb7890514322a25685c143017fbc
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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