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Tetrahydrofuran → Methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate

HRID 543855
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HRID 543855 반응식
[C:1]([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH2:9][CH2:10][C:11]([OH:13])=O)[CH2:4][CH2:5][C:6]([OH:8])=[O:7])#[N:2].Cl[C:21]1C=CC(C(C#N)(CCC(O)=O)CCC(O)=O)=CC=1.O1CCCC1.CC(C)([O-])C.[K+]>C(O)(=O)C>[C:6]([CH:5]1[CH2:4][C:3]([C:1]#[N:2])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:10][C:11]1=[O:13])([O:8][CH3:21])=[O:7]
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참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 2765824-Cyano-4-phenylheptanedioic acidHCID 204534054-(p-Chlorophenyl)-4-cyanopimelic acidHCID 23665647Potassium tert-butoxide

생성물 1

HCID 582396Methyl 5-cyano-2-oxo-5-phenylcyclohexanecarboxylate수율 60%

시약·촉매·용매 1

HCID 176
Acetic Acid
용매

실험 절차

Following the procedure of Preparation I, Part b, but substituting 2.0 gm. (0.0069 mole) of the dimethyl ester of 4-cyano-4-phenylpimelic acid (prepared in Part a, above) for the 34.97 gm. of the dimethyl ester of 4-(p-chlorophenyl)-4-cyanopimelic acid and using 45 ml. of the tetrahydrofuran, 1.57 gm. (0.014 mole) of the potassium tert-butoxide, and 10 ml. of the 2.5 N acetic acid instead of the 700 ml., the 24.4 gm., and the 175 ml., respectively, there is obtained a residue which upon recrystallization from technical hexane gives 1.07 gm. (60% yield) of the desired 2-carbomethoxy-4-cyano-4-phenylcyclohexanone having a melting point at 79.5° to 81.5° C.

후처리

  1. customthe procedure of Preparation I, Part b
  2. custom, respectively, there is obtained a residue which
  3. customupon recrystallization from technical hexane
  4. customgives 1.07 gm

출처 및 근거

ORD 기록
ord-e0712427d22c413b9d36ff7c166bc3da
출처 데이터셋
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04447454

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