Tetrahydrofuran → 3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-methylcyclohexanone

HRID 1660053Notes

Reaction equation

HRID 1660053 reaction equation
[Li].C[Cu]C.O1CCC[CH2:6]1.[CH2:10]([O:17][C:18]1[CH:23]=[C:22]([C:24]([CH3:32])([CH3:31])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:21]=[CH:20][C:19]=1[C:33]1[CH2:38][CH2:37][CH2:36][C:35](=[O:39])[CH:34]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+]>CCOCC>[CH2:10]([O:17][C:18]1[CH:23]=[C:22]([C:24]([CH3:31])([CH3:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:21]=[CH:20][C:19]=1[C:33]1([CH3:6])[CH2:38][CH2:37][CH2:36][C:35](=[O:39])[CH2:34]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 198553803-[2-Benzyloxy-4-(1,1-Dimethylheptyl)phenyl]cyclohex-2-enoneHCID 178477771HCID 178477771, compound

Product 1

HCID 204969083-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-3-methylcyclohexanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a -10° C. to -5° C. solution of 4.17 mmoles of dimethylcopper lithium in 10 ml. of tetrahydrofuran was slowly added 5.60 g. (1.39 mmoles) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohex-2-enone in 5 ml. of tetrahydrofuran. The reaction mixture was stirred for 30 minutes longer and was then added to 100 ml. of saturated ammonium chloride and 100 ml of ether. After stirring for 10 minutes the quenched reaction was extracted with 200 ml. of ether. The ether extract was washed with 100 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The oil was purified via preparative layer chromatography on three 20 cm.×20 cm.×2 mm. silica gel plates eluted with 2:1 cyclohexane:ether to yield 282 mg. (48%) (higher Rf) of the title compound, as an oil, and 211 mg. (36%) (lower Rf) of 3-[ 2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-methylcyclohex-2-en-1-ol, as an oil.

Workup

  1. customTo a -10° C. to -5° C.
  2. additionwas then added to 100 ml
  3. stirringAfter stirring for 10 minutes
  4. customthe quenched reaction
  5. extractionwas extracted with 200 ml
  6. extractionThe ether extract
  7. washwas washed with 100 ml
  8. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  9. customevaporated to an oil
  10. customThe oil was purified via preparative layer chromatography on three 20 cm
  11. washsilica gel plates eluted with 2:1 cyclohexane
  12. customether to yield 282 mg

Sources & evidence

ORD record
ord-de907ef030914043bfc28ea7d27a507b
Source dataset
uspto-grants-1981_12
Patent number
US04306097

Reaction notes

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