Sodium borohydride → HCID 86593314, compound

HRID 1610764Notes

Reaction equation

HRID 1610764 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10](=[O:29])[CH:11]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]3[O:25][CH2:24][C:23]([CH3:27])([CH3:26])[C:22]=3[CH:28]=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:29])[CH:11]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]3[O:25][CH2:24][C:23]([CH3:26])([CH3:27])[C:22]=3[CH:28]=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 22261468HCID 22261468, compound

Product 1

HCID 86593314HCID 86593314, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension (140 ml) of zinc chloride (9.90 g, 72.6 mmol) in ether was added sodium borohydride (5.50 g, 145.2 mmol) at room temperature, and the mixture was stirred as it was for 2 hrs. Insoluble material was filtered off, and to the filtrate was added a solution of ethyl 3-(3-chlorophenyl)-2-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-3-oxopropionate (14.04 g, 36.3 mmol) in ether (50 ml), and the mixture was stirred at room temperature for 1.5 hrs. The reaction was quenched with 3N hydrochloric acid, and the reaction mixture was diluted with ethyl acetate and washed with water and saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, 5:1) to give ethyl (2RS,3RS)-3-(3-chlorophenyl)-2-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-3-hydroxypropionate (12.07 g, 86%) as a pale-yellow oil.

Workup

  1. filtrationInsoluble material was filtered off
  2. stirringthe mixture was stirred at room temperature for 1.5 hrs
  3. customThe reaction was quenched with 3N hydrochloric acid
  4. additionthe reaction 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 under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, 5:1)

Sources & evidence

ORD record
ord-f51dc40ddddd40dc8c3e38a37e3ab0ab
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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