Nitrogen → 2-(2-(Chloromethyl)oxazol-4-yl)propan-2-ol

HRID 82833Notes

Reaction equation

HRID 82833 reaction equation
N#N.ClCC1OC=[C:8]([C:10]([O:12]C)=O)N=1.[CH3:14][Mg]Cl.[NH4+:17].[Cl-:18].[CH2:19]1[CH2:23][O:22][CH2:21][CH2:20]1>>[Cl:18][CH2:19][C:23]1[O:22][CH:21]=[C:20]([C:10]([OH:12])([CH3:8])[CH3:14])[N:17]=1

Participants

6

Reactant 5

HCID 947NitrogenHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 2763199Methyl 2-(chloromethyl)oxazole-4-carboxylateHCID 178418332HCID 178418332, compound

Product 1

HCID 679576962-(2-(Chloromethyl)oxazol-4-yl)propan-2-ol

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-(chloromethyl)oxazole-4-carboxylate (Organic Process Research & Development 2001, 5, 37-44) (13.00 g, 74.04 mmol) in THF (433 mL) was treated dropwise at 0° C. with methylmagnesium chloride (51.8 mL of a 3.0 M solution in THF, 155.49 mmol) and the resulting orange solution was stirred for 1.5 h at 0° C. The reaction mixture was carefully poured over an ice-chilled sat. aq. NH4Cl solution (300 mL). It was extracted with EA (3×200 mL) and the combined org. layers were washed with brine (300 mL), dried over MgSO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (6:4 hept-EA) gave the title compound as a yellow oil: TLC: rf (6:4 hept-EA)=0.24. LC-MS-conditions 06: tR=0.49 min.

Workup

  1. extractionIt was extracted with EA (3×200 mL)
  2. washlayers were washed with brine (300 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (6:4 hept-EA)

Sources & evidence

ORD record
ord-3e26a8cf26a94880a1fda5656f82ef25
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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