Sodium borohydride → 1050496-81-5

HRID 1011068Notes

Reaction equation

HRID 1011068 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:13])[CH2:9][CH:8]([CH2:10][CH:11]=[O:12])[CH2:7][CH2:6][O:5]1>C(O)C>[CH3:3][C:4]1([CH3:13])[CH2:9][CH:8]([CH2:10][CH2:11][OH:12])[CH2:7][CH2:6][O:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1261180774975-02-3

Product 1

HCID 576997271050496-81-5

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred suspension of sodium borohydride (0.620 g, 16.39 mmol) in dry ethanol (20 ml) was cooled to 0° C. (ice bath) under nitrogen and a solution of (2,2-dimethyltetrahydro-2H-pyran-4-yl)acetaldehyde (2.56 g, 16.39 mmol) in ethanol (20 ml) was added dropwise over a period of 20 mins. The mixture was then stirred in the cold for a further 1 hour then allowed to warm to ambient and stirred for 72 hours. The solvent was removed by evaporation and the residual oil was poured into ice and extracted with DCM (3×30 ml). Combined the organic extracts and dried by passing through a hydrophobic frit and evaporated in vacuo to give a colourless oil which contained the title compound.

Workup

  1. temperatureto warm to ambient and
  2. stirringstirred for 72 hours
  3. customThe solvent was removed by evaporation
  4. additionthe residual oil was poured into ice
  5. extractionextracted with DCM (3×30 ml)
  6. customdried
  7. customevaporated in vacuo
  8. customto give a colourless oil which

Sources & evidence

ORD record
ord-2ea50cc9bcfe4a178e9a91b4e3e9b197
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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