Dicyclohexylcarbodiimide → 2-[(E)-hex-2-enoyloxy]-5-(4'-hexylbiphenyl-4-yl)thiophene

HRID 2121307Notes

Reaction equation

HRID 2121307 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[S:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[CH:20][CH:21]=1.[C:40](O)(=[O:46])/[CH:41]=[CH:42]/[CH2:43][CH2:44][CH3:45]>CN(C)C1C=CN=CC=1.ClCCl>[C:40]([O:16][C:17]1[S:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[CH:20][CH:21]=1)(=[O:46])/[CH:41]=[CH:42]/[CH2:43][CH2:44][CH3:45]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 52827072-Hexenoic acid, (2E)-HCID 234321732-Hydroxy-5-(4'-hexylbiphenyl-4-yl)thiophene

Product 1

HCID 234321842-[(E)-hex-2-enoyloxy]-5-(4'-hexylbiphenyl-4-yl)thiopheneYield 49.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dicyclohexylcarbodiimide (0.4 g) is added to a solution of 2-hydroxy-5-(4′-hexylbiphenyl-4-yl)thiophene (0.25 g), (E)-hex-2-enoic acid, (0.2 g) 4-(dimethylamino)pyridine (0.10 g) and dichloromethane (50 cm3) at 0° C. under an atmosphere of nitrogen. The reaction mixture is stirred overnight at room temperature, filtered to remove inorganic material and the filtrate evaporated down. The residue is purified by column chromatography on silica gel using hexanelethyl acetate (9/1 v/v) as eluent and recrystallisation from hexane to yield 0.16 g of 2-[(E)-hex-2-enoyloxy]-5-(4′-hexylbiphenyl-4-yl)thiophene.

Workup

  1. filtrationfiltered
  2. customto remove inorganic material
  3. customthe filtrate evaporated down
  4. customThe residue is purified by column chromatography on silica gel using hexanelethyl acetate (9/1 v/v) as eluent
  5. customrecrystallisation from hexane

Sources & evidence

ORD record
ord-d1994db4896a418391c015b7f5dd9ecf
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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