Nitrogen → (2-(Chloromethyl)oxazol-4-yl)methanol
Reaction equation
N#N.[Cl:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10](OC)=[O:11])[N:9]=1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.CC(=O)OCC>[Cl:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([CH2:10][OH:11])[N:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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) (12.50 g, 71.20 mmol) in THF (400 mL) was treated dropwise at 0° C. with DiBAL-H (242 mL of a 1.0 M solution in THF, 242.0 mmol) and the resulting solution was stirred for 1 h at 0° C. and then allowed to warm to rt. The reaction mixture was carefully poured over a Rochelle's salt solution (600 mL) and EA (250 mL) was added. The mixture was stirred for 1.5 h. The aq. layer was extracted with EA (2×250 mL) and the combined org. layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (1:4 hept-EA) gave the title compound as a yellow oil: TLC: rf (1:4 hept-EA)=0.28. LC-MS-conditions 07: tR=0.39 min; [M+H]+=147.98.
Workup
- temperatureto warm to rt
- additionwas added
- stirringThe mixture was stirred for 1.5 h
- extractionThe aq. layer was extracted with EA (2×250 mL)
- dry with materiallayers were dried over MgSO4
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customPurification of the residue by FC (1:4 hept-EA)
Sources & evidence
- ORD record
- ord-1cf68b4e0d0b4a65bbfc8ec4d7fa7ede
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846733B2
Reaction notes
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