1-Propanol → HCID 67087083, compound

HRID 2365562Notes

Reaction equation

HRID 2365562 reaction equation
[C:1]1([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[CH2:17](O)[CH2:18][CH3:19].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CCOCC>[CH2:17]([O:10][C:9]([CH2:8][CH2:7][C:4]1[CH:3]=[CH:2][C:1]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1)=[O:11])[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 10311-PropanolHCID 10868DicyclohexylcarbodiimideHCID 779263,3'-(p-Phenylene)dipropionic acid

Product 1

HCID 67087083HCID 67087083, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,3′-(1,4-phenylene)dipropanoic acid (250 mg, 1.125 mmol) DCM (15 ml) is added 4-dimethylaminopyridine (137 mg, 1.125 mmol) and propanol (3 ml, 40.1 mmol). The solution is cooled to 0° C. and dicyclohexylcarbodiimide (232 mg, 1.125 mmol) is added and the resulting solution is stirred at 0° C. for 30 minutes and 2 hours at room temperature. Concentration in vacuo affords a white solid which is suspended in Et2O (50 ml) and filtered to remove any insoluble material. The filtrate is concentrated in vacuo and purification by chromatography (SiO2, EtOAc/iso-hexane) affords the title compound.

Workup

  1. concentrationConcentration in vacuo
  2. customaffords a white solid which
  3. filtrationfiltered
  4. customto remove any insoluble material
  5. concentrationThe filtrate is concentrated in vacuo and purification by chromatography (SiO2, EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-788544c2346147b3938dec2820895ddc
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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