Diethyl Ether → HCID 20496796, compound

HRID 1660058Notes

Reaction equation

HRID 1660058 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)-2-hydroxyphenyl]-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-492ec230516440489cbbb034ef1502ae
Source dataset
uspto-grants-1981_12
Patent number
US04306097

Reaction notes

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