Triethylamine → HCID 22852127, compound

HRID 1608756Notes

Reaction equation

HRID 1608756 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-c9de30509ce449d79bfdcb9621b6e927
Source dataset
uspto-grants-1995_03
Patent number
US05397775

Reaction notes

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