Lithium Hydroxide → HCID 11062693, compound

HRID 872683Notes

Reaction equation

HRID 872683 reaction equation
[Cl:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([C:8]([O:10]C)=[O:9])[N:7]=1.[OH-].[Li+]>C1COCC1.CO.O>[Cl:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([C:8]([OH:10])=[O:9])[N:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 2763199Methyl 2-(chloromethyl)oxazole-4-carboxylate

Product 1

HCID 11062693HCID 11062693, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 2-(chloromethyl)-1,3-oxazole-4-carboxylate (1.0 g, 5.70 mmol) was dissolved in THF/methanol mixture (9:1) and 1M lithium hydroxide (11.39 ml, 11.39 mmol) was added slowly. The reaction mixture was stirred at RT for 1 h, diluted with water and pH was adjusted to 2. The reaction mixture was extracted three times with ethyl acetate. Ethyl acetate phases were combined, dried and evaporated to dryness to yield the title compound (94%). 1H-NMR (400 MHz; DMSO3): δ 4.93 (s, 2H), 8.80 (s, 1H), 13.20 (bs, 1H).

Workup

  1. extractionThe reaction mixture was extracted three times with ethyl acetate
  2. customdried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-de9396ad73ce4f1db867484a8ddedf4b
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…