Acetic Acid → 4-(1methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acid

HRID 1980539노트

반응식

HRID 1980539 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17]([OH:20])(=[O:19])[CH3:18].C([O:24][C:25](=[O:27])C)(=O)C.P(=O)(O)(O)O>O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:3]2[CH2:11][CH2:12][C:18]([C:25]([OH:24])=[O:27])([C:17]([OH:20])=[O:19])[CH2:5][CH:4]=2)=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 770951-Methyl-2-phenylindole

생성물 1

HCID 134092844-(1methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acid수율 52%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 9.0 g (0.043 mol) of 1-methyl-2-phenylindole, 9.3 g (0.05 mol) 4,4-cyclohexanonedicarboxylic acid, 100 mL of acetic acid, 4.7 mL of acetic anhydride, and 1 mL of 85% phosphoric acid was stirred at room temperature for 17 h, and then 100 mL of water was added dropwise to give a white solid which was collected and washed with water. The solid was taken up in ether, washed with water three times and with brine two times, dried over magnesium sulfate, concentrated in vacuo, and crystallized from acetonitrile to give 8.4 g (52%) of 4-(1methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acid, m.p. 210°-211° C.

후처리

  1. customto give a white solid which
  2. customwas collected
  3. washwashed with water
  4. washwashed with water three times and with brine two times
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customcrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-a37511ea74ee4c9da4dee2d9b69eab44
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04510158

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