Tetrahydrofuran → 3,3,4-Trimethylpentan-1-ol

HRID 586141Notes

Reaction equation

HRID 586141 reaction equation
[CH3:1][C:2]([CH3:8])([CH:5]([CH3:7])[CH3:6])[CH:3]=[CH2:4].C1C[O:12]CC1>>[CH3:1][C:2]([CH3:8])([CH:5]([CH3:7])[CH3:6])[CH2:3][CH2:4][OH:12]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 5217093,3,4-Trimethylpent-1-ene

Product 1

HCID 124253343,3,4-Trimethylpentan-1-ol

Procedure

3,3,4-Trimethylpentene (1 equiv) is dissolved in dry THF under Ar. The reaction mixture is cooled to −78° C. at which time a 1 M solution of borane/dimethylsulfide complex in THF (0.4 equiv) is added dropwise. The cold bath is removed and the reaction mixture is allowed to warm to ambient temperature. The reaction mixture is carefully diluted with a solution of sodium acetate in aqueous hydrogen peroxide (large exess). The reaction mixture is stirred at ambient temperature and then diluted with diethyl ether and the layers are separated. The organic layer is dried over Na2SO4, decanted and concentrated. The crude material is purified by fractional distillation to yield 3,3,4-trimethylpentanol.

Workup

  1. additionis added dropwise
  2. customThe cold bath is removed
  3. additionThe reaction mixture is carefully diluted with a solution of sodium acetate in aqueous hydrogen peroxide (large exess)
  4. additiondiluted with diethyl ether
  5. customthe layers are separated
  6. dry with materialThe organic layer is dried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated
  9. distillationThe crude material is purified by fractional distillation

Sources & evidence

ORD record
ord-415ce4a83c8f4e548a44f745b8c0d24d
Source dataset
uspto-grants-2005_08
Patent number
US06936606B2

Reaction notes

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