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

HRID 709806Notes

Reaction equation

HRID 709806 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+]>CO>[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 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethyltetrahydro-2H-pyran-4-carbaldehyde (2.50 g) in methanol (15 mL) was slowly added at 0° C. sodium tetrahydroborate (3.30 g) by small portions, and the mixture was stirred at room temperature for 6 hr. The solvent was evaporated under reduced pressure, and saturated brine was added to the residue. The reaction mixture was extracted with dichloromethane, and the extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.50 g) as a pale-yellow oil. This compound was used for the next step without further purification.

Workup

  1. customThe solvent was evaporated under reduced pressure, and saturated brine
  2. additionwas added to the residue
  3. extractionThe reaction mixture was extracted with dichloromethane
  4. dry with materialthe extract was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f18d30402fe2454c8affa4ded821fb93
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…