Hydrochloric Acid → HCID 86593281, compound

HRID 1610624Notes

Reaction equation

HRID 1610624 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:28]=[CH:27][C:10]([CH2:11][CH:12]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Cl.O>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[C:3]([C:7]1[CH:28]=[CH:27][C:10]([CH2:11][CH:12]([CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[OH:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:5])[CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22262188HCID 22262188, compound

Product 1

HCID 86593281HCID 86593281, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (22.3 g, 163.6 mmol) in diethyl ether (500 ml) was added sodium borohydride (12.4 g, 327.2 mmol), and the mixture was stirred at room temperature for 30 min. Insoluble material was filtered off, and to the filtrate was added a solution of ethyl 2-(4-tert-butylbenzyl)-3-(3-chlorophenyl)-3-oxopropanoate (30.5 g, 81.8 mmol) in diethyl ether. (200 ml) at 0° C. The mixture was stirred for 30 min. and 1N hydrochloric acid was added to stop the reaction. Water (200 ml) was further added, and the mixture was extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine; dried (anhydrous magnesium sulfate) and evaporated under reduced pressure to give the objective substance (26.8 g, 87%).

Workup

  1. filtrationInsoluble material was filtered off
  2. customat 0° C
  3. stirringThe mixture was stirred for 30 min.
  4. customthe reaction
  5. extractionthe mixture was extracted with ethyl acetate (200 ml×2)
  6. washThe extract was washed with water and saturated brine
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. customevaporated under reduced pressure
  9. customto give the objective substance (26.8 g, 87%)

Sources & evidence

ORD record
ord-91ceb71c48a44b69a659ac93caa41f16
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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