Sodium borohydride → HCID 66978202, compound

HRID 655106Notes

Reaction equation

HRID 655106 reaction equation
[CH3:1][C:2]12[CH2:9][CH:6]([CH2:7][CH2:8]1)[CH:5]([CH3:10])[C:4](=[O:11])[CH2:3]2.[BH4-].[Na+]>C(O)(C)C>[CH3:1][C:2]12[CH2:9][CH:6]([CH2:7][CH2:8]1)[CH:5]([CH3:10])[CH:4]([OH:11])[CH2:3]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66974043HCID 66974043, compound

Product 1

HCID 66978202HCID 66978202, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1,4-Dimethyl-bicyclo[3.2.1]octan-3-one (325 g, 2.14 mol, obtained as above in EXAMPLE III) was added to a a NaBH4 suspension (24 g, 0.64 mol) in isopropanol (600 mL), and refluxed for 30 minutes. The reaction mixture was cooled to room temperature, and quenched with acetone followed by acetic acid. The organic layer was separated and concentrated to provide crude 1,4-dimethyl-bicyclo[3.2.1]octan-3-ol (300 g, 1.9 mol), which was added to a solution of sodium amide (NaNH2, 94 g, 2.4 mol) in tetrahydrofuran (THF, 1 L) while at reflux, and aged for 5 hours. Allyl chloride (CH2CHCH2Cl, 170 g, 2.2 mol) was subsequently added at 45° C. and aged for another 2 hours. The reaction mixture was subsequently washed with water and a Na2CO3 solution. Fractional distillation of the organic layer provided 3-allyloxy-1,4-dimethyl-bicyclo[3.2.1]octane (220 g) having a boiling point of 120° C. at a pressure of 30 mmHg

Workup

  1. temperaturerefluxed for 30 minutes
  2. customquenched with acetone
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f0f28029df674fed8e047baa87f0b223
Source dataset
uspto-grants-2011_12
Patent number
US08071529B1

Reaction notes

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