Acrylic Acid → HCID 18979511, compound

HRID 2392592Notes

Reaction equation

HRID 2392592 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[N:28][C:29]([C:32]2[CH:39]=[CH:38][C:35]([CH:36]=[O:37])=[CH:34][CH:33]=2)=[N:30][CH:31]=1.[C:40](O)(=[O:43])[CH:41]=[CH2:42]>CN(C)C1C=CN=CC=1.ClCCl>[C:40]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[N:28][C:29]([C:32]2[CH:39]=[CH:38][C:35]([CH:36]=[O:37])=[CH:34][CH:33]=2)=[N:30][CH:31]=1)(=[O:43])[CH:41]=[CH2:42]

Participants

6

Reactant 3

HCID 6581Acrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 18979503HCID 18979503, compound

Product 1

HCID 18979511HCID 18979511, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4.2 g of N,N'-dicyclohexylcarbodiimide were added within 5 minutes while stirring to a solution of 5.5 g of 4-(5-[8-hydroxyoctyloxy]pyrimidin-2-yl)benzaldehyde, 1.2 g of acrylic acid and 0.2 g of 4-(dimethylamino)pyridine in 25 ml of dichloromethane. The reaction mixture was stirred overnight, filtered and the filtrate was concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol of the fractions which were pure according to thin-layer chromatography gave 4.8 g of 4-(5-[8-acryloyloxyoctyloxy]pyrimidin-2-yl)benzaldehyde.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol of the fractions which

Sources & evidence

ORD record
ord-41ba35b8e873456fb6305dfff757eb3b
Source dataset
uspto-grants-1998_09
Patent number
US05800733

Reaction notes

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