Triethylsilane → HCID 68955700, compound

HRID 1514648Notes

Reaction equation

HRID 1514648 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([CH3:18])=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]=1[CH:24]=O)([CH3:4])([CH3:3])[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([CH3:18])=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]=1[CH3:24])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 86626938HCID 86626938, compound

Product 1

HCID 68955700HCID 68955700, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A 700 mg portion of ethyl 5-tert-butyl-4-formyl-2-methyl-1-(2-phenylethyl)-1H-pyrrole-3-carboxylate was dissolved in 21 ml of trifluoroacetic acid, mixed with 3.3 ml of triethylsilane at 0° C. and stirred for 2 hours while rising the temperature from 0° C. to room temperature. The solvent was evaporated under a reduced pressure, azeotropy with toluene was carried out, and then the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:50-1:40-1:30) to obtain 652 mg of ethyl 5-tert-butyl-2,4-dimethyl-1-(2-phenylethyl)-1H-pyrrole-3-carboxylate as a colorless oil.

Workup

  1. customfrom 0° C. to room temperature
  2. customThe solvent was evaporated under a reduced pressure, azeotropy with toluene
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:50-1:40-1:30)

Sources & evidence

ORD record
ord-ac6182ebfd7c4ea0b109049154136471
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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