Dicyclohexylcarbodiimide → HCID 178418275, 화합물

HRID 1639

반응식

HRID 1639 반응식
[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

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 21846715(E)-4-(trimethylsilyl)but-2-en-1-olHCID 178418479HCID 178418479, 화합물

생성물 1

HCID 178418275HCID 178418275, 화합물수율 38%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-998b94bdae2a4efb8c11261a196e92e3
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726191

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