Acetic Acid → t-Butyl 4-[2-(2-cyano-3-methoxy-2-cyclopentenyl)ethyl]benzoate

HRID 2294097노트

반응식

HRID 2294097 반응식
[C:1]([CH:3]1[CH:7]([CH2:8][CH2:9][C:10]2[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5][C:4]1=[O:23])#[N:2].[CH:24](N(CC)C(C)C)(C)C.C(O)(=O)C>CO.C(#N)C.CCCCCC>[C:1]([C:3]1[CH:7]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[CH:21][CH:22]=2)[CH2:6][CH2:5][C:4]=1[O:23][CH3:24])#[N:2]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 10470833t-Butyl 4-(2-(2-cyano-1-cyclopentanon-3-yl)ethyl]benzoate

생성물 1

HCID 10359093t-Butyl 4-[2-(2-cyano-3-methoxy-2-cyclopentenyl)ethyl]benzoate

시약·촉매·용매 2

HCID 8058Hexane용매HCID 21959252Acetonitrile methanol용매

실험 절차

t-Butyl 4-[2-(2-cyano-1-cyclopentanon-3-yl)-ethyl]benzoate (0.43 g, 1.37 mmol) prepared in the Preparative Example 105 and N,N-diisopropylethylamine (0.21 g, 1.64 mmol) were dissolved in a methanol/acetonitrile (1:5) mixture, followed by the addition of 3.2 g of a 10% by weight solution of trimethylsilyldlazomethane in hexane. The obtained mixture was stirred at room temperature for 2 hours, followed by the addition of a small amount of acetic acid. The mixture this obtained was stirred and distilled to remove the solvent. The residue was dissolved in diethyl ether, washed with diluted hydrochloric acid, dilute alkali ind an aqueous solution of common salt, dehydrated and concentrated to dryness. The residue was purified by silica gel column chromatography to give the objective compound. yield: 0.23 g

후처리

  1. stirringThe mixture this obtained was stirred
  2. distillationdistilled
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washwashed with diluted hydrochloric acid
  6. additiondilute alkali
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by silica gel column chromatography
  9. customto give the objective compound

출처 및 근거

ORD 기록
ord-e35299c00dfd46df91474b24e4abf21f
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05688800

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