Hydrochloric Acid → 4-[1-(hydroxy)-4,4-dimethyl-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

HRID 1607738Notes

Reaction equation

HRID 1607738 reaction equation
[CH3:1][C:2]([CH3:21])([CH2:17][CH2:18][CH2:19][CH3:20])[CH:3]=[CH:4][C:5]([CH:7]1[CH:14]2[CH:10]([O:11][C:12](=[O:15])[CH2:13]2)[CH2:9][CH:8]1[CH3:16])=[O:6].[BH4-].[Na+].Cl>CO>[OH:6][CH:5]([CH:7]1[CH:14]2[CH:10]([O:11][C:12](=[O:15])[CH2:13]2)[CH2:9][CH:8]1[CH3:16])[CH:4]=[CH:3][C:2]([CH3:1])([CH3:21])[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 731845924-(4,4-dimethyl-1-oxo-2-octenyl)hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

Product 1

HCID 731845934-[1-(hydroxy)-4,4-dimethyl-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The crude racemic (3aR,4S,5R,6aS)-[S*,R*-(E)]-rac-4-(4,4-Dimethyl-1-oxo-2-octenyl)hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one (10.0 g, 0.0342 mole) in methanol (150 mL) solution was cooled to 0° and treated with sodium borohydride (1.0 g, 0.0264 mole). After stirring for 1 hour at 0°, 3N HCl (15 mL) was added dropwise. The methanol was stripped off under reduced pressure using a 40° bath and the residue was partitioned between water and ether. The ether layer was washed with NaHCO3 solution and witb brine, dried over sodium sulfate and stripped of solvent. The residue of crude, racemic [3aR-[3a alpha,4alpha-(1S*,2E),5beta, 6a alpha]]-4-[1-(hydroxy)-4,4-dimethyl-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one was a viscous amber oil weighing 10.26 g (100%).

Workup

  1. customusing a 40°
  2. customthe residue was partitioned between water and ether
  3. washThe ether layer was washed with NaHCO3 solution
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-0817f2f82cf24918831fa2f0120e6433
Source dataset
uspto-grants-1989_09
Patent number
US04866205

Reaction notes

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