Sodium borohydride → HCID 22261585, compound

HRID 1610729Notes

Reaction equation

HRID 1610729 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([C:25]1[N:26]=[C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[S:28][CH:29]=1)[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:24])([F:23])[CH:20]([F:22])[F:21])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]>CCOCC.[Cl-].[Zn+2].[Cl-]>[OH:3][CH:4]([C:25]1[N:26]=[C:27]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[S:28][CH:29]=1)[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:23])([F:24])[CH:20]([F:22])[F:21])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22261823HCID 22261823, compound

Product 1

HCID 22261585HCID 22261585, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension (50 ml) of zinc chloride (3.41 g, 25 mmol) in ether was added sodium borohydride (1.89 g, 50 mmol) at room temperature, and the mixture was stirred as it was for 2 hrs. Insoluble material was filtered off. To the filtrate was added a solution of ethyl 3-oxo-3-(2-phenyl-1,3-thiazol-4-yl)-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propionate (6.01 g, 12.5 mmol) in ether (40 ml) under ice-cooling, and the mixture was stirred as it was for 1 hr. The reaction was quenched with 1N hydrochloric acid. The mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1, 4:1) to give ethyl 3-hydroxy-3-(2-phenyl-1,3-thiazol-4-yl)-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propionate (4.61 g, 76%) as a colorless transparent oil.

Workup

  1. filtrationInsoluble material was filtered off
  2. temperaturecooling
  3. stirringthe mixture was stirred as it
  4. waitwas for 1 hr
  5. customThe reaction was quenched with 1N hydrochloric acid
  6. additionThe mixture was diluted with ethyl acetate
  7. washwashed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1, 4:1)

Sources & evidence

ORD record
ord-01abeb2991a848ebb444126c9a69be05
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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