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

HRID 1755656ノート

反応式

HRID 1755656 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-methoxypropenoate (2.77 g, 40% yield) as a white crystalline solid, m.p. 67°-69° C. IR (nujol): 1710, 1634 cm-1. 1H NMR: delta 3.72 (3H, s), 3.84 (3H, s), 7.30-7.65 (3H, m), 7.69 (1H, s), 7.9 (1H, m), 10.0 (1H, s) ppm.

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-c6f00cc89feb481aa2812793272c265f
出典データセット
uspto-grants-1995_08
特許番号
US05438059

反応ノート

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