Chloroacetonitrile → 5-tert-Butyl-2-(chloromethyl)-1,3-oxazole

HRID 2085366Notes

Reaction equation

HRID 2085366 reaction equation
B(F)(F)F.CCOCC.[N+:10](=[CH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[N-].[Cl:19][CH2:20][C:21]#N>>[Cl:19][CH2:20][C:21]1[O:18][C:13]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:12][N:10]=1

Participants

4

Reactant 3

HCID 7856Chloroacetonitrile2×HCID 8000Boron trifluoride etherateHCID 217927841-Diazonio-3,3-dimethylbut-1-en-2-olate

Product 1

HCID 129689745-tert-Butyl-2-(chloromethyl)-1,3-oxazole

Conditions

Temperature
0 °C

Procedure

To a stirred solution of chloroacetonitrile (40 mL) and boron trifluoride etherate (20 mL, 0.16 mmol) at 0° C. was added 1-diazo-3,3-dimethyl-2-butanone in chloroacetonitrile (40 mL) dropwise over a period of 20 minutes. After addition was complete, the mixture was stirred at 0° C. for one hour and then partitioned between saturated NaHCO3, solution (700 mL) and CH2Cl2 (500 mL). The aqueous solution was extracted with CH2Cl2 (500 mL) and the combined organic layers were washed with brine (400 mL) and dried over MgSO4. After filtration, the solution was concentrated and then distilled under vacuum using an oil bath temperature of 40° C. The 2-(chloromethyl)-5-t-butyloxazole (9.2 g, 44% overall from the acid chloride, C8H12ClNO, MS m/e 174 (M+H)+) was obtained as a light yellow oil.

Workup

  1. additionAfter addition
  2. custompartitioned between saturated NaHCO3, solution (700 mL) and CH2Cl2 (500 mL)
  3. extractionThe aqueous solution was extracted with CH2Cl2 (500 mL)
  4. washthe combined organic layers were washed with brine (400 mL)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe solution was concentrated
  8. distillationdistilled under vacuum
  9. customtemperature of 40° C

Sources & evidence

ORD record
ord-ca75c1ac79204baebe7b3e7f89a7d04e
Source dataset
uspto-grants-2004_04
Patent number
US06720347B2

Reaction notes

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