Sodium borohydride → HCID 59518690, compound

HRID 1161634Notes

Reaction equation

HRID 1161634 reaction equation
[CH2:1]([C:6]1([CH:17]=[O:18])[CH2:11][CH2:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:8][O:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[BH4-].[Na+]>C(O)(C)C>[CH2:1]([C:6]12[O:7][CH:8]([O:18][CH2:17]1)[CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:10][CH2:11]2)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21694368HCID 21694368, compound

Product 1

HCID 59518690HCID 59518690, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
35 °C

Procedure

2,5-dipentyl-3,4-dihydro-2H-pyran-2-carbaldehyde (165 g, synthesized as above) was loaded in a 3-liter round bottom flask and dissolved in 500 mL of isopropanol. Sodium Borohydride (6.1 g, commercially available from Sigma-Aldrich Inc) was added and the reaction exothermed up to about 58° C. The reaction was then stirred for about 2 hours. The reaction mixture was periodically sampled and analyzed by GC to monitor the reaction progress. After GC indicated the consumption of about all the starting material, sulfuric acid (500 mL, 10% solution in water) was then added and the temperature was increased to 35° C. The reaction mixture was further stirred for about 30 minutes and then cooled. The organic layer was separated and washed with 500 mL 10% aqueous sodium hydroxide solution. The solvents were removed to yield the crude product, which was purified by distillation to provide 1,4-dipentyl-6,8-dioxa-bicyclo[3.2.1]octane (128 g).

Workup

  1. customexothermed up to about 58° C
  2. aliquotThe reaction mixture was periodically sampled
  3. customthe consumption of about all the starting material, sulfuric acid (500 mL, 10% solution in water)
  4. additionwas then added
  5. stirringThe reaction mixture was further stirred for about 30 minutes
  6. temperaturecooled
  7. customThe organic layer was separated
  8. washwashed with 500 mL 10% aqueous sodium hydroxide solution
  9. customThe solvents were removed
  10. customto yield the crude product, which
  11. distillationwas purified by distillation

Sources & evidence

ORD record
ord-d3f521b1b0524483892036233ba463ef
Source dataset
uspto-grants-2010_10
Patent number
US07820616B1

Reaction notes

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