Diethyl Ether → HCID 20496796, compound

HRID 1074478Notes

Reaction equation

HRID 1074478 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][C:18](=[O:22])[CH2:19][CH2:20][CH:21]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[BH4-].[Na+].[Cl-].[Na+].CCOCC>CO>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][CH:18]([OH:22])[CH2:19][CH2:20][CH:21]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 20496795HCID 20496795, compound

Product 1

HCID 20496796HCID 20496796, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a -18° C. solution of 17.5 g (50 mmol) of 3-[4-(1,1-dimethylheptyl)-2hydroxyphenyl]-cyclohex-3-enone in 50 ml of methanol is added 1.9 g (50 mmol) of sodium borohydride. The reaction mixture is stirred for 30 minutes and then added to 250 ml of saturated sodium chloride-250 ml of ether. The ether extract is washed once with 250 ml of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 400 g of silica gel eluted with 50% ether-pentane to yield the title compound.

Workup

  1. extractionThe ether extract
  2. washis washed once with 250 ml of saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue is purified via column chromatography on 400 g of silica gel
  6. washeluted with 50% ether-pentane

Sources & evidence

ORD record
ord-379c02456c3f4100bfd749a1c40f2161
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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