Ethyl Propionate → HCID 178514951、化合物

HRID 49889

反応式

HRID 49889 の反応式
C[O-].[Na+].[C:4]1(=[O:13])[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH2:6][O:5]1.[N:14]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1.C(OCC)(=O)CC>CO>[NH:14]1[CH:19]=[CH:18][C:17](=[C:20]2[C:6](=[O:5])[C:7]3[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=3[C:4]2=[O:13])[CH:16]=[CH:15]1

参加物

6

反応物 4

HCID 7749Ethyl PropionateHCID 133894-PyridinecarboxaldehydeHCID 10942334Sodium MethoxideHCID 125790144,5,6,7-Tetrahydro-2-benzofuran-1(3H)-one

生成物 1

HCID 178514951HCID 178514951、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Four portions each of 0.99 ml 5.4 M methanolic sodium methylate solution (21.4 mmol) are stirred into a solution of 2.957 g (21.4 mmol) 4,5,6,7-tetrahydro-1(3H)-isobenzofuranone (for preparation see J. Am. Chem. Soc. 118, 1-12 [1996]), 2.02 ml (21.4 mmol) pyridine-4-carbaldehyde, and 10.7 ml (93.2 mmol) ethyl propionate in 17.4 ml methanol at intervals of 5 min respectively and at 0° C. The reaction mixture is stirred for 20 min at RT, heated for 2 h under reflux, and then evaporated under vacuum. Stirring of the residue in 5 ml water, filtration, washing of the filter residue with water, and drying under HV (8 h, 100° C.) yields the title compound; m.p. 258-261° C.; ESI-MS: (M+H)+=228. A further, slightly impure batch of title compound may be obtained by extracting the aqueous filtrate with diethylether, adjusting the aqueous phase to pH 7 with glacial acetic acid, filtering, and washing the filter residue with water.

後処理

  1. customat 0° C
  2. temperatureheated for 2 h
  3. temperatureunder reflux
  4. customevaporated under vacuum
  5. stirringStirring of the residue in 5 ml water
  6. filtrationfiltration
  7. washwashing of the filter residue with water
  8. customdrying under HV (8 h, 100° C.)

出典と根拠

ORDレコード
ord-a04317dc604c4abf975d9a0e8fe5f4e4
出典データセット
uspto-grants-2004_03
特許番号
US06710047B2

関連ノート

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