Dicyclohexylcarbodiimide → HCID 178418275、化合物

HRID 1639

反応式

HRID 1639 の反応式
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3]/[CH:4]=[CH:5]/[CH2:6][OH:7].[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][N:12]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C)C=O>[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O:7][CH2:6]/[CH:5]=[CH:4]/[CH2:3][Si:2]([CH3:9])([CH3:8])[CH3:1])=[O:16])=[CH:13][N:12]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 21846715(E)-4-(trimethylsilyl)but-2-en-1-olHCID 178418479HCID 178418479、化合物

生成物 1

HCID 178418275HCID 178418275、化合物収率 38%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

1.3 g of 4-trimethylsilyl-(E)-but-2-en-1-ol (synthesis described in J. Org. Chem. 1984, 49, 4092), 1.08 g of 6-hydroxy-nicotinic acid and 178 mg of 4-dimethylaminopyridine were placed in succession in 30 ml of abs. dimethylformamide. 1.77 g (1.1 eq.) of dicyclohexylcarbodiimide were added thereto at 0° and the mixture was left to react at room temperature overnight. The separated urea was filtered off, the filtrate was extracted with ethyl acetate, washed twice with H2O, dried over Na2 SO4 and the solvent was removed under reduced pressure. Flash chromatography on SiO2 (hexane/ethyl acetate=1/1) yielded 782 mg of 4-trimethylsilanyl-(E)-but-2-enyl 6-hydroxy-nicotinate as white crystals of m.p. 107°-110° (dec.).

後処理

  1. waitat 0° and the mixture was left
  2. customto react at room temperature overnight
  3. filtrationThe separated urea was filtered off
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washwashed twice with H2O
  6. customdried over Na2 SO4
  7. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-998b94bdae2a4efb8c11261a196e92e3
出典データセット
uspto-grants-1998_03
特許番号
US05726191

関連ノート

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