Diethyl Ether → HCID 19759462, compound

HRID 1586805Notes

Reaction equation

HRID 1586805 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([CH2:17]O)[CH:14]=[C:13]2[C:19]#[N:20])=[CH:8][CH:7]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(OCC)C>ClCCl.CCCCCC>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]2[C:19]#[N:20])=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 19759235HCID 19759235, compound

Product 1

HCID 19759462HCID 19759462, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 1-(4-ethoxycarbonylphenyl)-4-hydroxymethylpyrrole-2-carbonitrile (500 mg) in dichloromethane (5.5 ml) was added trifluoroacetic acid (2.8 ml) and triethylsilane (652 μl) in that order at 5° C. under nitrogen. The mixture was stirred at 5° C. for one and half hours and at ambient temperature for one hour and then poured into a mixture of diethyl ether and n-hexane (1:1). The mixture was washed with saturated sodium bicarbonate solution and brine, dried, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution by ethyl acetate/n-hexane=1/10) to yield 1-(4-ethoxycarbonylphenyl)-4-methylpyrrole-2-carbonitrile (163 mg) as a white solid.

Workup

  1. washThe mixture was washed with saturated sodium bicarbonate solution and brine
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (elution by ethyl acetate/n-hexane=1/10)

Sources & evidence

ORD record
ord-060acc78aa124a4cb4e494a753870ac7
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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