Sodium borohydride → (2,2-Dimethyloxan-4-yl)methanol

HRID 1010985Notes

Reaction equation

HRID 1010985 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH:6]([CH:8]=[O:9])[CH2:5][CH2:4][O:3]1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1([CH3:10])[CH2:7][CH:6]([CH2:8][OH:9])[CH2:5][CH2:4][O:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 122319282,2-Dimethyloxane-4-carbaldehyde

Product 1

HCID 51072184(2,2-Dimethyloxan-4-yl)methanolYield 100.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,2-dimethyltetrahydro-2H-pyran-4-carbaldehyde (2.5 g) in ethanol (30 mL) was cooled (ice bath) and sodium borohydride (665 mg) was added with stirring. The ice bath was removed and the mixture was allowed to warm to room temperature. After 2 h the reaction was heated to 50° C. for 1 h, then allowed to cool to room temperature. The solvent was evaporated and the residue was treated with brine, acidified and extracted into DCM (×3). The combined organics were dried through a hydrophobic frit and evaporated to give a clear oil (2.54 g).

Workup

  1. additionwas added
  2. customThe ice bath was removed
  3. temperatureAfter 2 h the reaction was heated to 50° C. for 1 h
  4. temperatureto cool to room temperature
  5. customThe solvent was evaporated
  6. additionthe residue was treated with brine
  7. extractionextracted into DCM (×3)
  8. customThe combined organics were dried through a hydrophobic frit
  9. customevaporated

Sources & evidence

ORD record
ord-2a68b4b0d7e3446eb12a49e3808cc83f
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…