Nitrogen → 2-(Chloromethyl)-4-(2-methoxypropan-2-yl)oxazole

HRID 82834Notes

Reaction equation

HRID 82834 reaction equation
N#N.[Cl:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[N:9]=1.[CH3:14]I>>[Cl:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([O:13][CH3:14])([CH3:11])[CH3:12])[N:9]=1

Participants

4

Reactant 3

HCID 947NitrogenHCID 6328Methyl iodideHCID 679576962-(2-(Chloromethyl)oxazol-4-yl)propan-2-ol

Product 1

HCID 679581392-(Chloromethyl)-4-(2-methoxypropan-2-yl)oxazole

Conditions

Temperature
40 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(2-(chloromethyl)oxazol-4-yl)propan-2-ol (200 mg, 1.14 mmol) in MeI (3.5 mL) was treated with Ag2O (396 mg, 1.71 mmol) and the resulting mixture (protected from light) was stirred for 26 h at 40° C. The reaction mixture was filtered and the MeI was removed under reduced pressure. Purification of the residue by FC (7:3 hept-EA) gave the title compound as a colorless oil: TLC: rf (7:3 hept-EA)=0.33. LC-MS-conditions 06: tR=0.64 min, [M+H]+=190.17.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe MeI was removed under reduced pressure
  3. customPurification of the residue by FC (7:3 hept-EA)

Sources & evidence

ORD record
ord-37b6a07a220b4573a1a1a216b39a1522
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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