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

HRID 1074473노트

반응식

HRID 1074473 반응식
[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

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 25517Ammonium ChlorideHCID 198553803-[2-Benzyloxy-4-(1,1-Dimethylheptyl)phenyl]cyclohex-2-enoneHCID 178477771HCID 178477771, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-59c6bbc6bfac49148fc564fa8d5793b4
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04391827

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