Sodium borohydride → 1,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentanol

HRID 1390551

Reaction equation

HRID 1390551 reaction equation
[CH3:1][C:2]1([CH3:24])[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[CH2:9][CH2:10][C:11](=[O:23])[CH2:12][CH2:13][CH:14]1[C:19]([CH3:21])([CH3:20])[CH:18]2[CH2:22][CH:15]1[CH2:16][CH2:17]2.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1([CH3:24])[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[CH2:9][CH2:10][CH:11]([OH:23])[CH2:12][CH2:13][CH:14]1[C:19]([CH3:20])([CH3:21])[CH:18]2[CH2:22][CH:15]1[CH2:16][CH2:17]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 213328461,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentanone

Product 1

HCID 213328421,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ketone, 1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentanone (2 grams) was dissolved in 100 ml. of ethanol and stirred with 2 grams of sodium borohydride overnight. The solvent was removed in vacuo and the residue partitioned between ethyl ether and water. The organic layer was dried over sodium sulfate. After filtration, and removal of solvent a colorless oil was obtained that crystallized on standing, m.p. 55° C.-56° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl ether and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationAfter filtration, and removal of solvent a colorless oil
  5. customwas obtained
  6. customthat crystallized

Sources & evidence

ORD record
ord-8e660559ec5a4d1a89cdbf6e555f403d
Source dataset
uspto-grants-1979_02
Patent number
US04139559

Linked notes

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