Sodium borohydride → HCID 66934568, compound

HRID 1363948Notes

Reaction equation

HRID 1363948 reaction equation
[CH:1]1([C:9](=[O:12])[CH2:10][CH3:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[CH:1]1([CH:9]([OH:12])[CH2:10][CH3:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66956911HCID 66956911, compound

Product 1

HCID 66934568HCID 66934568, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-cyclooct-3-enylpropan-1-one (84.0 g, 0.5 mol) was slowly added to a solution of sodium borohydride (11.9 g, 0.3 mol) in ethanol (330 ml) at 0° C. (ice bath), and stirring was continued at room temperature for 4 h. The reaction mixture was poured into ice-cold 2N HCl (500 ml) and extracted with MTBE (2×200 ml). After washing with brine (3×200 ml), drying (MgSO4) and evaporation of solvents, the yellowish oily residue (86.6 g) was distilled over a 20 cm Widmer column (66-80° C./0.7-0.8 mbar) to give 69.2 g of 1-cyclooct-3-enylpropan-1-ol (colourless oil, 68% yield). It consisted of >90% of a 1:1 mixture of two diastereomeric racemates of 1-cyclooct-3-enylpropan-1-ol. An analytical sample was purified by flash chromatography (hexane/MTBE 3:1).

Workup

  1. extractionextracted with MTBE (2×200 ml)
  2. washAfter washing with brine (3×200 ml)
  3. customdrying
  4. custom(MgSO4) and evaporation of solvents
  5. distillationthe yellowish oily residue (86.6 g) was distilled over a 20 cm Widmer column (66-80° C./0.7-0.8 mbar)

Sources & evidence

ORD record
ord-9b8161262e8e4df7a85d7958b47f1cd1
Source dataset
uspto-grants-2011_02
Patent number
US07888309B2

Reaction notes

Loading…