(1-Ethoxymethylimidazol-2-yl)-4-methylphenylmethanone → 1-(Imidazol-2-yl)-1-(4-methylphenyl)-3-(1-pyrrolidyl)propane

HRID 2285736Notes

Reaction equation

HRID 2285736 reaction equation
C([Li])CCC.[Br-].[N:7]1([CH2:12][CH2:13][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.C(OC[N:37]1[CH:41]=[CH:40][N:39]=[C:38]1[C:42]([C:44]1[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=1)=O)C>CCCCCC.C1COCC1>[NH:37]1[CH:41]=[CH:40][N:39]=[C:38]1[CH:42]([C:44]1[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=1)[CH2:13][CH2:12][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 13019450(1-Ethoxymethylimidazol-2-yl)-4-methylphenylmethanoneHCID 19085441Phosphonium, triphenyl(2-(1-pyrrolidinyl)ethyl)-, bromide (1:1)HCID 178418339Butyllithium

Product 1

HCID 130194581-(Imidazol-2-yl)-1-(4-methylphenyl)-3-(1-pyrrolidyl)propaneYield 106.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of n-butyl lithium in hexane (1.6 M, 7.7 ml) was added dropwise under nitrogen with stirring to a suspension of 2-(1-pyrrolidyl)ethyltriphenylphosphonium bromide (5.41 g) in dry THF (75 ml) keeping the temperature at -10° to -5°. The addition was complete after 5 min. The mixture was then stirred at 0° for 20 min. then cooled to -5° and treated with a solution of (1-ethoxymethylimidazol-2-yl)-4-methylphenylmethanone (3.0 g) in dry THF (30 ml). The mixture was stirred at room temperature for 16 h. and then the precipitated triphenylphosphine oxide was filtered off and washed with a little THF (10 ml). The filtrate and washings were combined and concentrated in vacuo to a yellow syrup. This was absorbed from chloroform (3 ml) onto a column of silica gel (Merck Kieselgel 60, 200 g). Removal of the solvent afforded isomers of the title compound as a thick yellow brown syrup (3.52 g) which was used in the next stage without further purification.

Workup

  1. customat -10° to -5°
  2. additionThe addition
  3. temperaturethen cooled to -5°
  4. stirringThe mixture was stirred at room temperature for 16 h.
  5. filtrationthe precipitated triphenylphosphine oxide was filtered off
  6. washwashed with a little THF (10 ml)
  7. concentrationconcentrated in vacuo to a yellow syrup
  8. customThis was absorbed from chloroform (3 ml) onto a column of silica gel (Merck Kieselgel 60, 200 g)
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-39d36acbfc4b48208a783c2c532dfb48
Source dataset
uspto-grants-1982_04
Patent number
US04324792

Reaction notes

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