Sodium borohydride → HCID 67019977, compound

HRID 1662277Notes

Reaction equation

HRID 1662277 reaction equation
[CH2:1]([C:3](=[CH:6][CH2:7][C@H:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[C:9]1([CH3:15])[CH3:14])[CH:4]=[O:5])[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([C:3](=[CH:6][CH2:7][C@H:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[C:9]1([CH3:14])[CH3:15])[CH2:4][OH:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86640087HCID 86640087, compound

Product 1

HCID 67019977HCID 67019977, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Ethyl-4-[(1R)-2,2,3-trimethylcyclopentyl]but-2-enal (3a; 8.5 g, 41 mmol) was added dropwise within 10 min. to a stirred suspension of sodium borohydride (1.9 g, 50 mmol) in ethanol (100 ml) at 5-10° C. After additional 2 h stirring at room temperature, the reaction mixture was poured into an ice-cold 0.1 N HCl solution and extracted with MTBE (200 ml). The extract was washed with ice-cold brine (2×100 ml), dried (MgSO4), concentrated in vacuo and the residue was distilled under reduced pressure to give 2-ethyl-4-[(1R)-2,2,3-trimethylcyclopentyl]but-2-en-1-ol (4a) which was further purified by flash chromatography (MTBE/hexane 1:5; 5.8 g, 68% yield, colourless liquid; GC/MS: 2 isomeric pairs of enantiomers 0.5+88.5%).

Workup

  1. extractionextracted with MTBE (200 ml)
  2. washThe extract was washed with ice-cold brine (2×100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-989247a6776c4ce9b618db082c99250f
Source dataset
uspto-grants-2011_10
Patent number
US08030524B2

Reaction notes

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