Allyl bromide → HCID 19902096, compound

HRID 1493734Notes

Reaction equation

HRID 1493734 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[Cl:6][C:7]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:8]=1[CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.[CH:20](=[O:27])[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(Br)C=C>CCCCCC.O1CCCC1.O.C(Cl)Cl>[CH2:3]([O:27][CH:20]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH:9]([C:8]1[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:7]=1[Cl:6])[N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)[CH:2]=[CH2:1]

Participants

8

Reactant 4

HCID 7841Allyl bromideHCID 16275CyclohexanecarboxaldehydeHCID 3161266HCID 3161266, compoundHCID 178418339Butyllithium

Product 1

HCID 19902096HCID 19902096, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

33 ml (50 mmol) of n-butyllithium in hexane were added to 11.4 g (50 mmol) of N-(2,4-dichlorobenzyl)-imidazole in 100 ml of tetrahydrofuran at -78° C., stirring was continued for half an hour and 6.1 g (55 mmol) of hexahydrobenzaldehyde were then added dropwise. The mixture was kept at -70° C. for a further two hours, after which it was allowed to warm up to 0° C. and 6.7 g (55 mmol) of allyl bromide in 50 ml of tetrahydrofuran were added. The reaction mixture was then stirred for 15 hours at room temperature and worked up with water/methylene chloride. 19.8 g of a crude product were obtained in the form of an oil, from which 5.5 g of the imidazole derivative were isolated by column chromatography over silica gel using 4:1 cyclohexane/ethyl acetate.

Workup

  1. waitwas continued for half an hour
  2. stirringThe reaction mixture was then stirred for 15 hours at room temperature

Sources & evidence

ORD record
ord-85babd96768248548f002fe97337777c
Source dataset
uspto-grants-1991_06
Patent number
US05023357

Reaction notes

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