Dicyclohexylcarbodiimide → HCID 19757567, compound

HRID 1587264Notes

Reaction equation

HRID 1587264 reaction equation
[CH2:1]([C:9]1[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:17]([Si:21]([CH3:34])([CH3:33])[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)[CH2:18][CH2:19][CH3:20].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[CH2:1]([C:9]1[S:13][C:12]([C:14]([O:16][C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH2:23][CH2:22][Si:21]([CH2:17][CH2:18][CH2:19][CH3:20])([CH3:34])[CH3:33])=[CH:27][CH:28]=2)=[O:15])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 131282715-Octylthiophene-2-carboxylic acidHCID 19757561HCID 19757561, compound

Product 1

HCID 19757567HCID 19757567, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15 ml of dichloromethane was added to 0.38 g (1.58 mM) of 5-octylthiophene-2-carboxylic acid and 0.42 g (1.58 mM) of 4-[3-(butyldimethylsilyl)propoxy]phenol, followed by stirring at room temperature to the mixture, 0.31 g (1.50 mM) of N,N'-dicyclohexylcarbodiimide (DCC) and 0.02 g of 4-pyrrolidinopyridine were added, followed by stirring for 5 hours at room temperature. The resultant dicyclohexylurea was recovered by filtration, followed by washing with dichloromethane to be added to the filtrate. The resultant dichloromethane solution was condensed into a solid under reduced pressure, followed by purification by silica gel column chromatography (eluent: toluene) and recrystallization from ethanol to obtain 0.45 g of 4-[3-(butyldimethylsilyl)propoxy]phenyl 5-octylthiophene-2-carboxylate (Yield: 61.4 %). ##STR71##

Workup

  1. additionwere added
  2. filtrationThe resultant dicyclohexylurea was recovered by filtration
  3. washby washing with dichloromethane
  4. additionto be added to the filtrate
  5. customcondensed into a solid under reduced pressure
  6. customfollowed by purification by silica gel column chromatography (eluent: toluene) and recrystallization from ethanol

Sources & evidence

ORD record
ord-e464c2424f934b7391e0c3c1ddcffe35
Source dataset
uspto-grants-1993_06
Patent number
US05217645

Reaction notes

Loading…