Triethylamine → HCID 22852127, compound

HRID 2260834Notes

Reaction equation

HRID 2260834 reaction equation
O1CCCCC1[O:7][CH2:8][C@H:9]([C:11]1([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:10].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(N(CC)CC)C>C(O)C.C1(C)C=CC=CC=1>[OH:7][CH2:8][C@H:9]([C:11]1([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67732301HCID 67732301, compound

Product 1

HCID 22852127HCID 22852127, compoundYield 117%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2a (3.42 g, 15.0 mmol) and pyridinium p-toluenesulfonate (188 mg) in ethanol (100 mL) was heated at 40°-50° C. with stirring for 10 hr. The mixture was diluted with toluene and a small amount of triethylamine was added to the mixture. After evaporation of ethanol, the residue was poured into brine and extracted with ethyl acetate until none of the product remained the in aqueous layer. The combined organic layers were washed with brine, and dried over sodium sulfate. Filtration and concentration gave 2.53 g of an oily material, which was purified by column chromatography (silica gel 20 g, ethyl acetate in n-hexane, 20-50%) to give 1.88 g (86.9%) of 3a, as a colorless oil.

Workup

  1. temperaturewas heated at 40°-50° C.
  2. customAfter evaporation of ethanol
  3. additionthe residue was poured into brine
  4. extractionextracted with ethyl acetate until none of the product
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-c82f9b725f0145239774862c224b4a54
Source dataset
uspto-grants-1995_12
Patent number
US05478955

Reaction notes

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