Acetyl chloride → HCID 21849172, compound

HRID 617890Notes

Reaction equation

HRID 617890 reaction equation
[NH2:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)([CH2:5][OH:6])[CH2:3][OH:4].C(N(CC)CC)C.C(=O)=O.CO.[C:35](Cl)(=[O:37])[CH3:36]>C(O)C.C(Cl)(Cl)Cl.ClCCl>[C:35]([NH:1][C:2]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:12]=1)([CH2:5][OH:6])[CH2:3][OH:4])(=[O:37])[CH3:36]

Participants

8

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10566696HCID 10566696, compoundHCID 21973728Carbon dioxide methanol

Product 1

HCID 21849172HCID 21849172, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-Amino-2-(4-decylphenyl)-1,3-propanediol (313 mg) was dissolved in a mixed solvent of ethanol (20 ml) and chloroform (5 ml). Thereto was added triethylamine (0.4 ml) and the mixture was cooled to -60° C. with dry ice-methanol. Thereto was dropwise added a solution of acetyl chloride (0.12 ml) in dichloromethane (5 ml) under ice-cooling and the mixture was heated to room temperature. The solvent was distilled away and the residue was dissolved in ethyl acetate. The mixture was washed with brine, an aqueous dilute hydrochloric acid solution and an aqueous sodium hydrogencarbonate solution. The resultant mixture was dried over anhydrous sodium sulfate and the solvent was distilled away. The residue was purified by preparative thin layer chromatography (silica gel) and recrystallized from hexane to give 130 mg of the colorless, crystalline subject compound.

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled away
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe mixture was washed with brine
  5. dry with materialThe resultant mixture was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away
  7. customThe residue was purified by preparative thin layer chromatography (silica gel)
  8. customrecrystallized from hexane
  9. customto give 130 mg of the colorless, crystalline subject compound

Sources & evidence

ORD record
ord-7637bbbd02ec4ff1916d355c9ae064a6
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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