Diisobutylaluminumhydride → 10,11-Dihydro-2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 1872020

반응식

HRID 1872020 반응식
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1[CH:28]=[CH:27][C:15]2[C:16](=[O:26])[C:17]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:18]=3[CH2:19][CH2:20][C:14]=2[CH:13]=1>O1CCCC1>[CH3:11][C:12]1[CH:28]=[CH:27][C:15]2[CH:16]([OH:26])[C:17]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:18]=3[CH2:19][CH2:20][C:14]=2[CH:13]=1

참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 2211720110,11-dihydro-2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-one

생성물 1

HCID 1868974710,11-Dihydro-2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Diisobutylaluminium hydride (5.5 ml of a 1M solution in tetrahydrofuran) was added dropwise to 10,11-dihydro-2,8-dimethyl-5H-dibenzo[a,d]cyclohepten-5-one (European Patent, 1993, 0 589 322 A1) (1.2 g) in tetrahydrofuran (20 ml) at-78 ° C. After 1 hour the cooling bath was removed and the reaction was stirred at r.t. for 2 hours. The reaction was quenched with brine and methanol. After 0.5 hours the reaction was partitioned between ethyl acetate and water. The ethyl acetate solution was washed with water, brine, dried (MgSO4) and evaporated. Purification was by chromatography eluting with toluene. Yield 1.2 g. Used directly in step (ii)

후처리

  1. customAfter 1 hour the cooling bath was removed
  2. customThe reaction was quenched with brine and methanol
  3. customAfter 0.5 hours the reaction was partitioned between ethyl acetate and water
  4. washThe ethyl acetate solution was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification
  8. washeluting with toluene

출처 및 근거

ORD 기록
ord-e02be76acde146da86d947344c9547d5
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06107297

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