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

HRID 2294097ノート

反応式

HRID 2294097 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 21959252Acetonitrile methanol溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-e35299c00dfd46df91474b24e4abf21f
出典データセット
uspto-grants-1997_11
特許番号
US05688800

反応ノート

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