Imidazole → HCID 20336128, compound

HRID 1706506Notes

Reaction equation

HRID 1706506 reaction equation
[Br:1]/[CH:2]=[CH:3]/[CH:4]([OH:14])[C:5]([CH3:13])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].CCOCC.N1C=CN=C1.[CH3:25][Si:26](Cl)([CH3:28])[CH3:27]>O1CCCC1>[Br:1]/[CH:2]=[CH:3]/[CH:4]([O:14][Si:26]([CH3:28])([CH3:27])[CH3:25])[C:5]([CH3:6])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:13]

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 20336140HCID 20336140, compound

Product 1

HCID 20336128HCID 20336128, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.8 g. of 1-bromo-4-methyl-4-phenyl-trans-1-pentene-3-ol in a mixture of 45 ml. of ether and 15 ml. of tetrahydrofuran was treated with 4.2 g. of imidazol under N2. After imidazol dissolved completely, the solution was treated at 0° with 5 ml. of trimethylsilyl chloride and stirred for one hour. The solvents were evaporated at 25° and the residue was diluted with n-pentane. After passing through an alumina column, the n-pentane filtrate was evaporated at 25° to afford 9.0 g. of the title product as a colorless liquid, λmaxfilm 3.45, 6.15, 6.65, 6.90, 7.20, 7.30, 7.98, 8.90, 9.10, 9.22, 10.60, 11.30, 11.85, 13.14 and 14.25 μ.

Workup

  1. additionthe solution was treated at 0° with 5 ml
  2. customThe solvents were evaporated at 25°
  3. additionthe residue was diluted with n-pentane
  4. customthe n-pentane filtrate was evaporated at 25°
  5. customto afford 9.0 g

Sources & evidence

ORD record
ord-ee79a533dcb440609339948c0773b88e
Source dataset
uspto-grants-1980_06
Patent number
US04207419

Reaction notes

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