Sodium borohydride → HCID 15592688, compound

HRID 2309228Notes

Reaction equation

HRID 2309228 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1)=[O:4].[BH4-].[Na+]>C(O)C>[O:11]([C:7]1[N:6]=[C:5]([CH:3]([C:2]([F:19])([F:1])[F:18])[OH:4])[CH:10]=[CH:9][CH:8]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14074439HCID 14074439, compound

Product 1

HCID 15592688HCID 15592688, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10.0 g (0.0375 mol) of the 2,2,2-trifluoro-1-(6-phenoxy-2-pyridinyl)ethanone of Step B in 100 ml of ethanol at 0° C. was added 1.5 g (0.0395 mol) of sodium borohydride portionwise over 5 to 10 minutes. The reaction was then warmed to room temperature and stirred overnight. After this time, the reaction was quenched with 1N aqueous HCl, neutralized with aqueous NaHCO3 and extracted with chloroform. The chloroform extracts were dried over MgSO4, filtered and concentrated to afford a yellow oil which solidified on standing to a waxy solid. Recrystallization from 4:1 hexane-ether afforded 6.13 g (60%) of the title compound as a white powder: m.p. 75° to 77° C.; 1H NMR (CDCl3) δ 4.67 (d, 1H), 4.92 (dq, 1H), 6.9-7.5 (m, 7H), 7.78 (t, 1H); IR (Nujol) 1570, 1600, 3390 cm-1.

Workup

  1. customAfter this time, the reaction was quenched with 1N aqueous HCl
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a yellow oil which
  7. customRecrystallization from 4:1 hexane-ether

Sources & evidence

ORD record
ord-40e107017dec487f8d261ba6876c0827
Source dataset
uspto-grants-1987_09
Patent number
US04694013

Reaction notes

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