Dicyclohexylcarbodiimide → HCID 178418275, compound

HRID 619318

Reaction equation

HRID 619318 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 178418275HCID 178418275, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

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 Na2SO4 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.).

Workup

  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. dry with materialdried over Na2SO4
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-842961ecf3dc405b8d1b2cda340d3665
Source dataset
uspto-grants-1999_09
Patent number
US05958956

Linked notes

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