Dicyclohexylcarbodiimide → 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentylthiophene

HRID 2121294Notes

Reaction equation

HRID 2121294 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=2)=[CH:19][CH:18]=1.[C:33](O)(=[O:39])/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH3:38]>CN(C)C1C=CN=CC=1.ClCCl>[C:33]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:26][CH:27]=2)=[CH:19][CH:18]=1)(=[O:39])/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 52827072-Hexenoic acid, (2E)-HCID 234323142-(4-Hydroxyphenyl)-5-pentylthiophene

Product 1

HCID 234321012-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentylthiopheneYield 56.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Dicyclohexylcarbodiimide (0.2 g) was added to a solution of 2-(4-hydroxyphenyl)-5-pentylthiophene (0.25 g), (E)-hex-2-enoic acid, (0.1 g) 4-(dimethyiamino)pyridine (0.05 g) and dichloromethane (20 cm3) at 0° C. under an atmosphere of nitrogen. The reaction mixture was stirred overnight at room temperature, filtered to remove inorganic material and the filtrate evaporated down. The residue was purified by column chromatography on silica gel using hexane/ethyl acetate (9/1 v/v) as eluent and recrystallisation from hexane to yield 0.17 g of 2-(4-[(E)-hex-2-enoyloxy]phenyl)-5-pentylthiophene, K 47° C., [N 46° C.], I.

Workup

  1. filtrationfiltered
  2. customto remove inorganic material
  3. customthe filtrate evaporated down
  4. customThe residue was purified by column chromatography on silica gel
  5. customrecrystallisation from hexane

Sources & evidence

ORD record
ord-3b185206e91f4394aba6b510eed36546
Source dataset
uspto-grants-2004_02
Patent number
US06696110B1

Reaction notes

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