Diethyl Ether → HCID 20558992, compound

HRID 1660059Notes

Reaction equation

HRID 1660059 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH:17]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]C.[BH4-].[Na+].[Cl-].[Na+].CCOCC>CO>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:21][CH2:20][CH2:19][CH:18]([OH:22])[CH:17]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 127882083-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenone

Product 1

HCID 20558992HCID 20558992, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a -18° C. solution of 70.0 g (0.20 mol) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-cyclohex-2-enone in 200 ml of methanol is added 7.6 g (0.20 mol) of sodium borohydride. The reaction mixture is stirred for 30 minutes and then added to one liter of saturated sodium chloride-one liter of ether. The ether extract is washed once with 500 ml of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 500 g of silica gel eluted with 50% ether-pentane to yield the title compound.

Workup

  1. extractionThe ether extract
  2. washis washed once with 500 ml of saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue is purified via column chromatography on 500 g of silica gel
  6. washeluted with 50% ether-pentane

Sources & evidence

ORD record
ord-9947a3fe3f9740d38faf26da79502148
Source dataset
uspto-grants-1981_12
Patent number
US04306097

Reaction notes

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