Sodium borohydride → HCID 86593315, compound

HRID 1610771Notes

Reaction equation

HRID 1610771 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10](=[O:31])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:30])([F:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:20][CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1>CCOCC.[Cl-].[Zn+2].[Cl-]>[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]([OH:31])[CH:11]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:30])([F:29])[C:25]([CH3:26])([CH3:28])[CH3:27])=[CH:22][CH:23]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22262034HCID 22262034, compound

Product 1

HCID 86593315HCID 86593315, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension (70 ml) of zinc chloride (4.94 g, 36.2 mmol) in ether was added sodium borohydride (2.74 g, 72.4 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-(3-chlorophenyl)-2-[4-(1,1-difluoro-2,2-dimethylpropyl)benzyl]-3-oxopropionate (7.59 g, 18.1 mmol) in ether (50 ml), and the mixture was stirred at room temperature for 1 hr. The reaction was quenched with 1N hydrochloric acid, and the mixture was diluted with ethyl acetate, washed with water and saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1, 10:1, 5:1) to give ethyl (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(1,1-difluoro-2,2-dimethylpropyl)benzyl]propionate (6.12 g, 80%) as a pale-yellow oil.

Workup

  1. filtrationInsoluble material was filtered off
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. customThe reaction was quenched with 1N hydrochloric acid
  4. additionthe mixture was diluted with ethyl acetate
  5. washwashed with water and saturated brine
  6. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1, 10:1, 5:1)

Sources & evidence

ORD record
ord-7035febfdad046ef90c20b012f11262d
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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