Hydrochloric Acid → HCID 18947423, compound

HRID 1769250Notes

Reaction equation

HRID 1769250 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].N1C=CN=C1.Cl>CO.C(OCC)C.O1CCCC1>[Si:20]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 1046616-Hydroxyhexadecanoic acidHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 18947423HCID 18947423, compoundYield 98.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

50 ml of a dry tetrahydrofuran solution containing 1 g of 16-hydroxyhexadecanoic acid, 1.1 g of tert-butyldimethylsilyl chloride and 0.75 g of imidazole, was stirred at room temperature for 12 hours under an inert atmosphere of nitrogen gas. The solvent was distilled off under reduced pressure, and then 200 ml of ethyl acetate was added. The mixture was washed three times with 200 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a syrup product. Then, 40 ml of diethyl ether, 30 ml of methanol and 30 ml of 1N hydrochloric acid were added thereto, and the mixture was stirred at room temperature for 15 minutes. The solvent was distilled off under reduced pressure, and then 200 ml of ethyl acetate was added. The mixture was washed once with 200 ml of a saturated sodium hydrogencarbonate aqueous solution and then washed twice with 200 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a syrup product. This product was purified by silica gel column chromatography (ethyl acetate: hexane =1:1) to obtain 1.4 g of 16-tert-butyldimethylsilyloxyhexadecanoic acid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. addition200 ml of ethyl acetate was added
  3. washThe mixture was washed three times with 200 ml of a saturated sodium chloride aqueous solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain a syrup product
  7. stirringthe mixture was stirred at room temperature for 15 minutes
  8. distillationThe solvent was distilled off under reduced pressure
  9. addition200 ml of ethyl acetate was added
  10. washThe mixture was washed once with 200 ml of a saturated sodium hydrogencarbonate aqueous solution
  11. washwashed twice with 200 ml of a saturated sodium chloride aqueous solution
  12. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  13. distillationthe solvent was distilled off under reduced pressure
  14. customto obtain a syrup product
  15. customThis product was purified by silica gel column chromatography (ethyl acetate: hexane =1:1)

Sources & evidence

ORD record
ord-dfbc21b017614bb5b7f0ceafc445d8b1
Source dataset
uspto-grants-1995_01
Patent number
US05380834

Reaction notes

Loading…