Dicyclohexylcarbodiimide → HCID 89477928, compound

HRID 1483194Notes

Reaction equation

HRID 1483194 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]#[C:12][C:13]([OH:15])=[O:14])[CH:8]=[CH:9][CH:10]=1)=[O:4].[Br:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20](O)=[CH:19][C:18]=1[CH3:25].C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C1C=CN=CC=1.ClCCl>[Br:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([O:14][C:13](=[O:15])[C:12]#[C:11][C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH3:1])=[O:4])=[CH:19][C:18]=1[CH3:25]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 819704-Bromo-3,5-dimethylphenolHCID 89477838HCID 89477838, compound

Product 1

HCID 89477928HCID 89477928, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a stirring solution of 3-(3-methoxycarbonylphenyl)propiolic acid (9-2) (102 mg, 0.50 mmol), 4-bromo-3,5-dimethylphenol (103 mg, 0.51 mmol) and 4-(dimethylamino)pyridine (12 mg, 0.10 mmol) in dichloromethane (2 mL) was added a solution of DCC (114 mg, 0.55 mmol) in dichloromethane (1 mL) under ice-cooling. The mixture was stirred under ice-cooling for 30 min then stirred at room temperature for 18 h. The mixture was diluted with dichloromethane filtered through a pad of Celite. The filtrate was evaporated to dryness, which was chromatographed on a silica gel (dichloromethane:hexanes=2:3) to give title compound 9-3 (95 mg, 49% yield) as a white solid.

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 min
  3. stirringthen stirred at room temperature for 18 h
  4. filtrationfiltered through a pad of Celite
  5. customThe filtrate was evaporated to dryness, which
  6. customwas chromatographed on a silica gel (dichloromethane:hexanes=2:3)

Sources & evidence

ORD record
ord-b6d2836050a54e0694203fb2b235e982
Source dataset
uspto-grants-2016_08
Patent number
US09416121B2

Reaction notes

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