Water → (E)-methyl 2-(2-formylphenyl)-3-methoxypropenoate

HRID 480553ノート

反応式

HRID 480553 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].P([O-])([O-])(O)=[O:18].[Na+].[Na+].P([O-])([O-])(O)=O.[K+].[K+].O>CS(C)=O>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11])=[O:18]

参加物

6

反応物 4

HCID 962WaterHCID 24203Sodium Phosphate, DibasicHCID 24450Potassium Phosphate, DibasicHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate

生成物 1

HCID 22872991(E)-methyl 2-(2-formylphenyl)-3-methoxypropenoate収率 40%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A mixture of (E)-methyl 2-[2-(bromomethyl)phenyl]-3-methoxypropenoate (10.0 g, 90% pure), sodium hydrogen orthophosphate dibasic (Na2HPO4, 5.74 g) and potassium hydrogen monophosphate monobasic (KH2PO4, 0.55 g) in DMSO (20 ml) was heated at 80° C. for 1 hour and then at 110° C. for a further hour (compare J H Babler, M J Coghlan, M Feng and P Fries, J.Org.Chem., 1979, 44, 1716). After cooling, the reaction mixture was poured into water and extracted with ether. The extracts were washed with brine, dried, concentrated and chromatographed using ether as eluant to give (E)-methyl 2-(2-formylphenyl)-3-methoxy-propenoate (2.77 g, 40% yield) as a white crystalline solid, m.p. 67-69° C.

後処理

  1. waitat 110° C. for a further hour (compare J H Babler, M J Coghlan, M Feng and P Fries, J.Org.Chem., 1979, 44, 1716)
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. washThe extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customchromatographed

出典と根拠

ORDレコード
ord-e9f839aad4bf479f95bac33258ecca2d
出典データセット
uspto-grants-2003_11
特許番号
US06653258B1

反応ノート

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