Sodium borohydride → HCID 66825503, compound

HRID 705867Notes

Reaction equation

HRID 705867 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[CH:6]=[O:7].[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:21])[F:20])[CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86666204HCID 86666204, compound

Product 1

HCID 66825503HCID 66825503, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(methyloxy)-4-{[3-(trifluoromethyl)phenyl]oxy}benzaldehyde (720 mg, 2.430 mmol) in ethanol (20 mL) was added slowly NaBH4 (110 mg, 2.92 mmol) at 0° C. The mixture was then allowed to warm to room temperature and stirring continued for 2 h. The reaction was quenched with NH4Cl sat. solution and extracted with EA. The organic layer was separated and concentrated to afford the title compound (715 mg, 2.397 mmol, 99% yield). LCMS: rt=3.12 min, [M+H+−H2O]=281

Workup

  1. customThe reaction was quenched with NH4Cl sat. solution
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-879082be8a064797aa39dcdaa3815e3e
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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