Water → 3,4-Dihydro-2,5-dimethyl-2H-pyran-2-methanol

HRID 2166647Notes

Reaction equation

HRID 2166647 reaction equation
[BH4-].[Na+].O.[CH3:4][C:5]1([CH:12]=[O:13])[CH2:10][CH2:9][C:8]([CH3:11])=[CH:7][O:6]1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.CC(C)=O>[CH3:4][C:5]1([CH2:12][OH:13])[CH2:10][CH2:9][C:8]([CH3:11])=[CH:7][O:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 159773,4-Dihydro-2,5-dimethyl-2H-pyran-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 981443,4-Dihydro-2,5-dimethyl-2H-pyran-2-methanol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

3.12 g of sodium borohydride was added to a rapidly stirred mixture of 140 ml of ether and 70 ml of water under a nitrogen atomosphere. To the resulting solution, a solution of 21.0 g of 3,4-dihydro-2,5-dimethyl-2H-pyran-2-carboxaldehyde (U.S. Pat. No. 2,479,283) in 42 ml of ether was added drop by drop. After 30 minutes, 21 ml of acetone was added. After 5 more minutes, the mixture was doubled in volume with a saturated solution of potassium carbonate and extracted with ether. The extract was washed with saturated sodium chloride solution, dried (sodium sulfate) and stripped of solvent to give 3,4-dihydro-2,5-dimethyl-2H-pyran-2-methanol (12A), as a pale green liquid, b.p.: not determined.

Workup

  1. extractionextracted with ether
  2. washThe extract was washed with saturated sodium chloride solution
  3. dry with materialdried (sodium sulfate)

Sources & evidence

ORD record
ord-e8a2567494bd4f3a9670a203c1aab64a
Source dataset
uspto-grants-1983_06
Patent number
US04388104

Reaction notes

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