Water → HCID 58307564, compound

HRID 1516453Notes

Reaction equation

HRID 1516453 reaction equation
[F:1][C:2]1[C:3]([OH:18])=[C:4]([CH2:11][CH2:12]OS(C)(=O)=O)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C(N(CC)CC)C.O>C(OCC)(=O)C>[F:1][C:2]1[C:3]2[O:18][CH2:12][CH2:11][C:4]=2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 58307565HCID 58307565, compound

Product 1

HCID 58307564HCID 58307564, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 6 (3.5 g, 12.53 mmol) in ethyl acetate (45 mL) and triethyl amine (4.37 mL, 31.33 mmol) was refluxed overnight. Water was added and the crude was extracted with ethyl acetate. The organic layer was concentrated, purified by column chromatography eluted with 15% ethyl acetate/hexane, to yield the desired compound 7 (1.4 g, yield 61%).

Workup

  1. temperaturewas refluxed overnight
  2. extractionthe crude was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by column chromatography
  5. washeluted with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9e3cf86c6e1248608bd87340547e4fa2
Source dataset
uspto-grants-2012_07
Patent number
US08227501B2

Reaction notes

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