Hydrochloric Acid → HCID 86593236, compound

HRID 1610343Notes

Reaction equation

HRID 1610343 reaction equation
[F:1][C:2]1([F:27])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][CH:12]([C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][C:4]=2[O:3]1.Cl>C(OCC)C.[BH4-].[Zn+2].[BH4-]>[F:27][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][CH:12]([CH:18]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[OH:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22262225HCID 22262225, compound

Product 1

HCID 86593236HCID 86593236, compound

Reagents, catalysts & solvents 2

HCID 12838295ZINC;boranuideCatalystHCID 3283Diethyl EtherSolvent

Procedure

While stirring zinc chloride (3.50 g, 25.7 mmol) in diethyl ether (50 ml), sodium borohydride (1.94 g, 51.4 mmol) was added at room temperature and the mixture was stirred as it was for 2 hrs. The insoluble material of the mixture was removed by filtration and washed with diethyl ether to give a solution of zinc borohydride in diethyl ether. To the obtained solution was added a solution of ethyl 2-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-3-(4-fluorophenyl)-3-oxopropionate (4.888 g, 12.85 mmol) in diethyl ether (30 ml) at room, temperature and the mixture was stirred as it was for 2 hrs. To the reaction solution was added dilute hydrochloric acid by small portions to decompose excess zinc borohydride and the mixture was extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated-under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1) to give the objective substance.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  3. customThe obtained crude product
  4. customwas purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1)
  5. customto give the objective substance

Sources & evidence

ORD record
ord-d6783e5399a14e7cbf3e7f9e15ed8ca9
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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