Hexane → HCID 67554916, compound

HRID 741726Notes

Reaction equation

HRID 741726 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:11]2[CH:28]=[CH:27][C:14]3[C:15](=[O:26])[C:16]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:17][O:18][C:13]=3[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2].[BH4-].[Na+].[Cl-].[NH4+].CCCCCC>CO.CCOCC>[C:1]([C:5]1[CH:6]=[C:7]([C:11]2[CH:28]=[CH:27][C:14]3[C:15]([OH:26])=[C:16]([CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:17][O:18][C:13]=3[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2]

Participants

7

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 21479421HCID 21479421, compound

Product 1

HCID 67554916HCID 67554916, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of the compound of step G (6.50 g, 17.5 mmole) in 35 mL of methanol at room temperature was added sodium borohydride (940 mg, 26.0 mmole) in one portion. The dark mixture was stirred at room temperature for 2 hours then poured into saturated aqueous ammonium chloride solution (75 mL) and extracted with 3×75 mL of diethyl ether. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give an off-yellow oil. Chromatography on silica gel eluting with 4:1 hexane: ether afforded first 3.26 g of the cis ring isomer of the title compound, and then 1.98 g of the trans isomer of the title compound as viscous oils, total yield 81%.

Workup

  1. extractionextracted with 3×75 mL of diethyl ether
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an off-yellow oil

Sources & evidence

ORD record
ord-fe8f68697d5c41198419fc495f151bdd
Source dataset
uspto-grants-1996_09
Patent number
US05552435

Reaction notes

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