Tetrahydrofuran → 4-Cyano-5-methyl-4-phenylhexanol

HRID 433656Notes

Reaction equation

HRID 433656 reaction equation
[C:1]([C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:5][C:6](O)=[O:7])#[N:2].O1CCCC1.C(=O)([O-])O.[Na+]>CO>[C:1]([C:3]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH:9]([CH3:10])[CH3:11])[CH2:4][CH2:5][CH2:6][OH:7])#[N:2]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 516892Sodium BicarbonateHCID 9837536HCID 9837536, compound

Product 1

HCID 101306314-Cyano-5-methyl-4-phenylhexanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-25 °C

Procedure

A 4-cyano-5-methyl-4-phenylhexanoic acid (500 mg, 2.16 mmol)/tetrahydrofuran (3.84 ml) solution was slowly added dropwise into a 1M-borane tetrahydrofuran complex/tetrahydrofuran solution (2.70 ml, 2.70 mmol) cooled to −25° C., while keeping the bulk temperature at −15° C. or less. After the completion of the dropwise addition, the bulk temperature was elevated to room temperature. After the completion of the reaction, it was cooled again and methanol (0.33 ml) was added dropwise thereinto. Further, a saturated aqueous sodium hydrogen carbonate solution (200 ml) was added thereinto, followed by extracting with ethyl acetate. The organic layer was successively washed with water, brine and saturated aqueous sodium hydrogen carbonate, followed by drying over magnesium sulfate and evaporating the solvent. The residue was purified by 20 g of Cromatorex NH silica gel (ethyl acetate/hexane system), to give the title compound as a colorless highly viscous oil (426 mg, 1.96 mmol, yield: 90.8%).

Workup

  1. customat −15° C. or less
  2. additionAfter the completion of the dropwise addition
  3. customwas elevated to room temperature
  4. customAfter the completion of the reaction, it
  5. temperaturewas cooled again
  6. extractionby extracting with ethyl acetate
  7. washThe organic layer was successively washed with water, brine and saturated aqueous sodium hydrogen carbonate
  8. dry with materialby drying over magnesium sulfate
  9. customevaporating the solvent
  10. customThe residue was purified by 20 g of Cromatorex NH silica gel (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-2858dfb4c93745b9801f66e24530fc65
Source dataset
uspto-grants-2003_12
Patent number
US06667412B1

Reaction notes

Loading…