Nitrogen → Ethyl 2-(hydroxymethyl)oxazole-4-carboxylate

HRID 1044769Notes

Reaction equation

HRID 1044769 reaction equation
N#N.[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH:13]=[O:14])[O:11][CH:12]=1)=[O:7])[CH3:4].[BH4-].[Na+].[NH4+].[Cl-]>CCO>[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:13][OH:14])[O:11][CH:12]=1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10583255Ethyl 2-formyl-1,3-oxazole-4-carboxylate

Product 1

HCID 10511369Ethyl 2-(hydroxymethyl)oxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), 2-formyl-oxazole-4-carboxylic acid ethyl ester (272 mg, 1.61 mmol) was dissolved in EtOH (5.0 mL). NaBH4 (112 mg, 2.84 mmol) was added portionwise at 0° C. and the reaction mixture stirred at 0° C. for 1 h. Sat. aq. NH4Cl was added and the mixture extracted with EA (5×10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. TLC: rf (EA)=0.50. LC-MS-conditions 02: tR=0.58 min; [M+H]+=172.03.

Workup

  1. extractionthe mixture extracted with EA (5×10 mL)
  2. dry with materialextracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-431b2e2a95a24881851ff677bbfe47b4
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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