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Water → 1-(Hydroxymethyl)-6-iodo-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 132999
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HRID 132999 반응식
[I:1][C:2]1[C:7]2[C:8](=[O:21])[C:9]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17](OC)=[O:18])[C:10]=3[CH:11]=[CH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.C(OCC)(=O)C>O1CCCC1.C1(C)C=CC=CC=1>[OH:18][CH2:17][C:13]1[C:10]2[CH:11]=[CH:12][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([I:1])[C:7]=3[CH:8]([OH:21])[C:9]=2[CH:16]=[CH:15][CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 58646834Methyl 6-iodo-5-oxo-5H-dibenzo[a,d]cycloheptene-1-carboxylate2회

생성물 1

HCID 586468371-(Hydroxymethyl)-6-iodo-5H-dibenzo[a,d]cyclohepten-5-ol

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 8028Tetrahydrofuran용매

실험 절차

50 mg of the mixture of methyl 6-iodo-5-oxo-5H-dibenzo[a,d]cycloheptene-1-carboxylate and its 4-iodo form prepared in Example 6-d was dissolved in 5 ml of dry tetrahydrofuran, and 0.75 ml of a 1M solution of diisobutyl aluminium hydride in toluene was added at room temperature. To the reaction mixture was added with small amounts of water and ethyl acetate, followed by stirring at room temperature for 30 minutes. Then, the reaction mixture was filtered through Celite, washed with ethyl acetate, and the solvent was removed, to give 40 mg of a mixture of the title compound with its 4-iodo form as a colorless powder.

후처리

  1. filtrationThen, the reaction mixture was filtered through Celite
  2. washwashed with ethyl acetate
  3. customthe solvent was removed

출처 및 근거

ORD 기록
ord-50c5691165a9496abce6efe3cd922400
출처 데이터셋
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07390797B2

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