(Diethylamino)sulfur trifluoride → HCID 15690213, compound

HRID 234706Notes

Reaction equation

HRID 234706 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 dilution 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); 1H-NMR (CD3Cl) δ1.215~1.219 (6H, m) 3.526 (2H, dm, J=15.3 Hz), 3.642~3.670 (2H, m), 3.680~3.808 (2H, m), 4.514 (1H, dm, J=45.9 Hz) ppm.

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. extractionAfter dichloromethane extraction
  5. dry with materialthe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified with silica gel column chromatography (hexane:ether=9:1, volume/volume)

Sources & evidence

ORD record
ord-d705a8b6e1ba49b3906b63f2de60d6e9
Source dataset
uspto-grants-1997_01
Patent number
US05596005

Reaction notes

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