Imidazole → HCID 10608197, compound

HRID 1746344Notes

Reaction equation

HRID 1746344 reaction equation
[CH:1](/[OH:6])=[CH:2]/[CH2:3][CH2:4][OH:5].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)Cl>[Si:12]([O:6][CH2:1]/[CH:2]=[CH:3]\[CH2:4][OH:5])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12584955HCID 12584955, compound

Product 1

HCID 10608197HCID 10608197, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of cis-1,4-butene diol (6) (20.0 g, 227.27 mmol) in dry CH2Cl2 (700 mL) at 0° C. was added imidazole (23.21 g, 340.91 mmol) and tert-butyldimethylsilyl chloride (37.68 g, 250.0 mmol). The reaction mixture was stirred at 0° C. for 6 h. After completion of reaction (monitored by TLC), it was diluted with CH2Cl2 (500 mL) washed with water, brine and dried over anhydrous Na2SO4. Removal of solvent under reduced pressure gave the crude product which was then purified by column chromatography with petroleum ether/EtOAc (9:1 v/v) to give (7) as a colorless liquid.

Workup

  1. customAfter completion of reaction (monitored by TLC), it
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customRemoval of solvent under reduced pressure
  5. customgave the crude product which
  6. customwas then purified by column chromatography with petroleum ether/EtOAc (9:1 v/v)

Sources & evidence

ORD record
ord-f660bd18544a4548bae25860b68bf1ce
Source dataset
uspto-grants-2015_10
Patent number
US09150498B2

Reaction notes

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