Formaldehyde → HCID 67376231、化合物

HRID 1677598ノート

反応式

HRID 1677598 の反応式
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[CH:8][CH:7]=1)[CH3:2].C=O.[C:26](=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:23])[C:5]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])=[CH:8][CH:7]=1)=[CH2:26])[CH3:2]

参加物

6

反応物 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 67375141HCID 67375141、化合物

生成物 1

HCID 67376231HCID 67376231、化合物収率 45%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 1140Toluene溶媒

実験手順

A solution of 2-(4-(benzyloxycarbonylamino)phenyl)ethanoic acid ethyl ester (6.5 g, 23.3 mmol), paraformaldehyde (1.05 g), potassium carbonate (5.15 g, 37.3 mmol) and tetrabutylammonium iodide (0.172 g, 0.5 mmol) in 230 mL of toluene was heated at 100° C. for 4 hours with stirring. The reaction mixture was filtered and the filtrate was washed with water, 1 M sodium hydrogen sulfate, and brine. The organic layer was evaporated in vacuo to afford 5.2 g of crude product. The product was purified by flash chromatography through silica gel (5/1 hexanes/ethyl acetate) to afford 2-(4-(benzyloxycarbonylamino)phenyl)prop-2-enoic acid ethyl ester 3.04 g (45%) as a white solid.

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with water, 1 M sodium hydrogen sulfate, and brine
  3. customThe organic layer was evaporated in vacuo
  4. customto afford 5.2 g of crude product
  5. customThe product was purified by flash chromatography through silica gel (5/1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-55c6815e406d494fa62006eba3df088d
出典データセット
uspto-grants-2011_08
特許番号
US08008325B2

反応ノート

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