(Diethylamino)sulfur trifluoride → HCID 86635272, compound

HRID 1013477Notes

Reaction equation

HRID 1013477 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([P:13]([O:17][CH3:18])([O:15][CH3:16])=[O:14])(O)[CH3:11])=[CH:6][CH:5]=1.CCN(S(F)(F)[F:26])CC>>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([P:13]([O:17][CH3:18])([O:15][CH3:16])=[O:14])[CH2:11][F:26])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 57925876HCID 57925876, compound

Product 1

HCID 86635272HCID 86635272, compound

Conditions

Temperature
-78 °C

Procedure

4-[1-(Dimethoxy-phosphoryl)-1-hydroxy-ethyl]-benzoic acid methyl ester (0.60 g, 2.08 mmol) was added over 30 minutes to a stirring solution of DAST (1M in CH2Cl2) cooled to −78° C. under a dry nitrogen environment. The mixture was warmed to ambient temperature and stirred. After stirring for 90 minutes the reaction mixture was carefully quenched with ethanol containing pyridine (pyr: twice volume of DAST). After stirring for 30 mins the mixture was poured into ice cold water and extracted into DCM (3×). The combined organic extracts were washed with dilute HCl, water, brine, dried (MgSO4) then concentrated in vacuo. The material was carried forward without further purification. MS: cal'd 291 (MH+), exp 291 (MH+)

Workup

  1. temperatureThe mixture was warmed to ambient temperature
  2. stirringAfter stirring for 90 minutes the reaction mixture
  3. customwas carefully quenched with ethanol
  4. additioncontaining pyridine (pyr: twice volume of DAST)
  5. stirringAfter stirring for 30 mins the mixture
  6. additionwas poured into ice cold water
  7. extractionextracted into DCM (3×)
  8. washThe combined organic extracts were washed with dilute HCl, water, brine
  9. dry with materialdried (MgSO4)
  10. concentrationthen concentrated in vacuo
  11. customThe material was carried forward without further purification

Sources & evidence

ORD record
ord-6b89f72c976c4fd3a6bf6b33501dff80
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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