Dicyclohexylcarbodiimide → 3-(2,4,5-Trifluorophenyl)propyl-3-(5-trimethylsilyl-3-furyl)proprionate

HRID 345897Notes

Reaction equation

HRID 345897 reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[C:3]1[O:7][CH:6]=[C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:4]=1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=1[CH2:24][CH2:25][CH2:26]O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[F:15][C:16]1[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=1[CH2:24][CH2:25][CH2:26][O:11][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[C:3]([Si:2]([CH3:1])([CH3:13])[CH3:14])[O:7][CH:6]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 199916093-(2,4,5-Trifluorophenyl)propan-1-olHCID 199916153-(5-Trimethylsilyl-3-furyl)propionic acid

Product 1

HCID 199915883-(2,4,5-Trifluorophenyl)propyl-3-(5-trimethylsilyl-3-furyl)proprionate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(5-trimethylsilyl-3-furyl)propionic acid (61.3 mg, 0.29 mmol), 3-(2,4,5-trifluorophenyl)propan-1-ol (55 mg, 0.29 mmol), 1,3-dicyclohexylcarbodiimide (66 mg, 0.32 mmol) and 4-dimethylaminopyridine (10 mg) in dichloromethane (3 ml) was stirred at room temperature overnight (17 hours). Most of the solvent was evaporated and the residue was purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane). The title ester was obtained as a colorless oil.

Workup

  1. customMost of the solvent was evaporated
  2. customthe residue was purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane)

Sources & evidence

ORD record
ord-53e0dda9298646e2b5636d95420fe3e6
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

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