Dicyclohexylcarbodiimide → HCID 21917263, compound

HRID 2242771Notes

Reaction equation

HRID 2242771 reaction equation
[I:1][C:2]1[S:6][C:5]([CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.[CH2:17]=[CH:18][CH:19](O)[CH:20]=[CH2:21].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:18]([CH:19]([O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][C:5]1[S:6][C:2]([I:1])=[CH:3][CH:4]=1)[CH:20]=[CH2:21])=[CH2:17]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 70204Penta-1,4-dien-3-olHCID 58720921HCID 58720921, compound

Product 1

HCID 21917263HCID 21917263, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-[5-iodo-(2-thienyl)]methoxyhexanoic acid (13.20 g, 37.3 mmol), 1,4-pentadien-3-ol (3.13 g, 37.3 mmol), dicyclohexylcarbodiimide (7.70 g, 37.3 mmol) and 4-dimethylaminopyridine (0.1 g) in DCM (250 mL) is stirred for 12 h under nitrogen. The solid is removed by filtration and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica, eluting with petroleum ether/diethyl ether (90:10), to give the product as a brown oil (12.27 g, 77%) NMR showed the expected signals.

Workup

  1. customThe solid is removed by filtration
  2. customthe filtrate is evaporated under reduced pressure
  3. customThe residue is purified by column chromatography on silica
  4. washeluting with petroleum ether/diethyl ether (90:10)

Sources & evidence

ORD record
ord-de8f424ddfab452e9219c8ea0161b045
Source dataset
uspto-grants-2010_03
Patent number
US07674397B2

Reaction notes

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