(Diethylamino)sulfur trifluoride → HCID 57515856, compound

HRID 1921932Notes

Reaction equation

HRID 1921932 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([CH3:15])(O)[CH3:13])=[N:9][CH:10]=1.CCN(S(F)(F)[F:22])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:22][C:12]([CH3:15])([CH3:13])[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 57515854HCID 57515854, compound

Product 1

HCID 57515856HCID 57515856, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1-(5-(methoxymethoxy)pyridin-2-yl)-2-methylpropan-2-ol (7.600 g, 36.0 mmol) was dissolved in 200 ml CH2Cl2 and cooled to −78° C. DAST (9.51 ml, 72.0 mmol) was added drop wise to the solution and stirring was continued for 30 min The mixture was allowed to warm up to 0° C. and was hydrolyzed with NaHCO3 (200 ml). Stirring was continued in the cold until gas evolution had ceased and the phases were separated. The aqueous was extracted 2× with EtOAc and the combined organic layers were dried over MgSO4 and evaporated. Glass col. Chromatography of the crude material provided 2-(2-fluoro-2-methylpropyl)-5-(methoxymethoxy)pyridine (5.80 g, 75.6% yield) as a pale yellow oil.

Workup

  1. temperatureto warm up to 0° C.
  2. stirringStirring
  3. customthe phases were separated
  4. extractionThe aqueous was extracted 2× with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-0b11921bc74148bb8c44fc0f29d0b99d
Source dataset
uspto-grants-2012_05
Patent number
US08173810B2

Reaction notes

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