HCID 22261246, compound → HCID 22261247, compound

HRID 348274Notes

Reaction equation

HRID 348274 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:17])=[C:11]([CH2:13][C:14](O)=[O:15])[N:12]=2)[CH:5]=[CH:6][CH:7]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:17])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 22261246HCID 22261246, compound

Product 1

HCID 22261247HCID 22261247, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(3-bromophenyl)-5-methyl-4-oxazoleacetic acid (39.1 g, 0.13 mol) in dry THF (175 mL) was treated dropwise with borane-THF complex (227 mL of a 1.0 M solution in THF, 1.3 mol) over 2 h (reaction temperature to 35° C.). After stirring 2 h at room temperature under N2, the reaction was quenched with slow addition of methanol (60 mL) and stirred overnight at room temperature. The reaction was diluted with 1 N NaOH (50 mL) and extracted with CH2Cl2 (2×200 mL). The organic layer was washed with H2O (3×100 mL), dried (MgSO4), and the solvent removed in vacuo to give 38.7 g of crude product that was recrystallized from toluene (200 mL, wash solid with cold hexanes) to give 26.9 g (72%) of 2-(3-bromophenyl)-5-methyl-4-oxazoleethanol as a white powder.

Workup

  1. custom(reaction temperature to 35° C.)
  2. customthe reaction was quenched with slow addition of methanol (60 mL)
  3. stirringstirred overnight at room temperature
  4. additionThe reaction was diluted with 1 N NaOH (50 mL)
  5. extractionextracted with CH2Cl2 (2×200 mL)
  6. washThe organic layer was washed with H2O (3×100 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed in vacuo
  9. customto give 38.7 g of crude product that
  10. customwas recrystallized from toluene (200 mL, wash solid with cold hexanes)

Sources & evidence

ORD record
ord-1f1bae5a4c6e4ff0a41d659064bc4ff4
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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