Imidazole → HCID 14234521, compound

HRID 35719Notes

Reaction equation

HRID 35719 reaction equation
[CH3:1][C@H:2]([CH2:8][CH2:9][OH:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].N1C=CN=C1.CN(C)C=O.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>O>[CH3:1][C@H:2]([CH2:8][CH2:9][O:10][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 10558755methyl (3R)-5-hydroxy-3-methylpentanoate

Product 1

HCID 14234521HCID 14234521, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 37 g. (0.253 m) of methyl 3-(R)-methyl-5-hydroxypentanoate and 37 g. (0.543 m) of imidazole in 500 ml. of dimethylformamide was added 37 g. (0.249 m) of t-butyldimethylsilyl chloride and the reaction stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted (4×100 ml.) with ether. The combined extracts were washed with 10% hydrochloric acid, a saturated sodium bicarbonate solution, water and a brine solution, and dried over magnesium sulfate. Removal of the solvent gave 121.88 g. of crude product which, on distillation, gave 107.12 g. of pure product, b.p. 80°-81° C./0.4 torr.

Workup

  1. extractionextracted (4×100 ml.) with ether
  2. washThe combined extracts were washed with 10% hydrochloric acid
  3. dry with materiala saturated sodium bicarbonate solution, water and a brine solution, and dried over magnesium sulfate
  4. customRemoval of the solvent
  5. customgave 121.88 g
  6. distillationof crude product which, on distillation
  7. customgave 107.12 g

Sources & evidence

ORD record
ord-b11ab87eeb784a5c8afeb9e91ddc813e
Source dataset
uspto-grants-1988_08
Patent number
US04767743

Reaction notes

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