Acetone → HCID 19879231, compound

HRID 1885594Notes

Reaction equation

HRID 1885594 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH2:22]([N-]CC)C.[Li+].C([Li])[CH2:29][CH2:30][CH3:31].C[Si](CCl)(C)C.CC(C)=O>O1CCCC1.O>[CH3:22][C:30]([CH3:29])=[CH:31][S:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 180AcetoneHCID 75361Silane, (chloromethyl)trimethyl-HCID 11137085Lithium diethylamide2×HCID 135962046(4-mercaptophenyl) 3 (4-pyridyl) 6,7dihydro[5H]-pyrrolo[1,2-a]imidazoleHCID 178418339Butyllithium

Product 1

HCID 19879231HCID 19879231, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 5 g (17 mmoles) of 2-(4-mercaptophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]-imidazole in dry tetrahydrofuran is treated at -20° C. with a solution of 17 mmoles of lithium diethylamide from 6.8 ml of 2.5 M n butyl lithium. After warming, a solution of 1.57 g (17 mmoles) of trimethylsilylmethylchloride in tetrahydrofuran is added dropwise. When the reaction is complete, the mixture is immersed in an ice bath and a second solution (17 mmoles) of lithium diethylamide is added. After stirring for 15 minutes, a solution of 0.99 g (17 mmoles) of acetone in tetrahydrofuran is added, and the mixture is stirred 15 minutes at 0° and 15 minutes at 25° C. The mixture is poured into water, extracted with methylene chloride, and the organic layer dried, and chromatographed on silica to afford the desired titled compound.

Workup

  1. temperatureAfter warming
  2. customthe mixture is immersed in an ice bath
  3. stirringthe mixture is stirred 15 minutes at 0° and 15 minutes at 25° C
  4. extractionextracted with methylene chloride
  5. customthe organic layer dried
  6. customchromatographed on silica

Sources & evidence

ORD record
ord-6ded54d448e1437c8043aa3546590d41
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

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