Imidazole → HCID 54125133, compound

HRID 703690Notes

Reaction equation

HRID 703690 reaction equation
[OH:1][C@@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20].N1C=CN=C1.O>CN(C=O)C>[O:1]([C@@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 11021563(S)-Methyl 3-hydroxytetradecanoate

Product 1

HCID 54125133HCID 54125133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.9 g of methyl (S)-3-hydroxytetradecanoate are dissolved in 50 ml of DMF under argon 9.0 g of t-butyldimethylchlorosilane are added thereto, 8.5 g of imidazole are then added portionwise and the mixture is left to stir for 17 hours. The reaction mixture is poured into 300 ml of water and extracted three times with 50 ml of diethyl ether. The combined organic phases are dried, filtered and evaporated. By distillation at 140°-145° C./0.07 mm there is obtained methyl (S)-3-(t-butyldimethylsiloxy)tetradecanoate as a colourless oil.

Workup

  1. additionare added
  2. waitthe mixture is left
  3. extractionextracted three times with 50 ml of diethyl ether
  4. customThe combined organic phases are dried
  5. filtrationfiltered
  6. customevaporated
  7. distillationBy distillation at 140°-145° C./0.07 mm there

Sources & evidence

ORD record
ord-e69bdbfec3d94c208e29eeb7e1582426
Source dataset
uspto-grants-1991_01
Patent number
US04983746

Reaction notes

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