(Diethylamino)sulfur trifluoride → HCID 15690213, compound

HRID 564891Notes

Reaction equation

HRID 564891 reaction equation
[CH2:1]([O:3][CH:4]([O:11][CH2:12][CH3:13])[CH:5](O)[CH2:6][N:7]=[N+:8]=[N-:9])[CH3:2].C(N(S(F)(F)[F:20])CC)C>C1C=CC=CC=1>[CH2:1]([O:3][CH:4]([O:11][CH2:12][CH3:13])[CH:5]([F:20])[CH2:6][N:7]=[N+:8]=[N-:9])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 11074181HCID 11074181, compound

Product 1

HCID 15690213HCID 15690213, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirring solution of 3-azido-2-hydroxypropanal diethyl acetal (7.32 g, 38.73 mmol) in dry benzene (50 mL) was added diethylaminosulfurtrifluoride (DAST; 20.6 mL) at −78° C. After the addition, the solution was stirred at room temperature for an hour, then heated to 70° C. for 12 hours. The reaction was quenched by the addition of methanol at zero degrees C and diluted with water. After dichloromethane extraction, the organic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified with silica gel column chromatography (hexane: ether=9:1, volume/volume) to yield 3-azido-2-fluoropropanal diethyl acetal as an oil (65 percent); Rf=0.84 EtOAc: hexane=2:3).

Workup

  1. additionAfter the addition
  2. temperatureheated to 70° C. for 12 hours
  3. customThe reaction was quenched by the addition of methanol at zero degrees C
  4. additiondiluted with water
  5. extractionAfter dichloromethane extraction
  6. dry with materialthe organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified with silica gel column chromatography (hexane: ether=9:1, volume/volume)

Sources & evidence

ORD record
ord-429960b07ffe4326a9e208eae1845d17
Source dataset
uspto-grants-2001_01
Patent number
US06168934A

Reaction notes

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