Diethyl Ether → HCID 21849306, compound

HRID 1451609Notes

Reaction equation

HRID 1451609 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([NH:15][C:16]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]([OH:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])([CH2:22][O:23][C:24](=[O:26])[CH3:25])[CH2:17][O:18][C:19](=[O:21])[CH3:20])(=[O:14])[CH3:13].CCOCC.S([O-])([O-])(=O)=O.[Mg+2]>ClCCl>[C:12]([NH:15][C:16]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34](=[O:41])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])([CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:22][O:23][C:24](=[O:26])[CH3:25])(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21849325HCID 21849325, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 21849306HCID 21849306, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (301.5 mg) was added to a solution of 2-acetamido-1,3-diacetoxy-2-(8-hydroxytetradecyl)propane (300 mg) in dichloromethane (19 ml) and the mixture was stirred at room temperature for 2 hours in a stream of nitrogen. Ether (38 ml) and magnesium sulfate (appropriate amount) were added thereto and the mixture was stirred for 10 minutes. The reaction mixture was suction-filtered and the filtrate was concentrated. The concentrate was extracted with ethyl acetate and the ethyl acetate layer was washed with 1N hydrochloric acid, a saturated sodium hydrogencarbonate solution and saturated brine in order. The resultant mixture was dried over magnesium sulfate. The solvent was distilled away to give the subject compound (290 mg).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. filtrationThe reaction mixture was suction-filtered
  3. concentrationthe filtrate was concentrated
  4. extractionThe concentrate was extracted with ethyl acetate
  5. washthe ethyl acetate layer was washed with 1N hydrochloric acid
  6. dry with materialThe resultant mixture was dried over magnesium sulfate
  7. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-8dcc1f07a2cf4bd398be341e080890af
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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