Water → HCID 22033413, compound

HRID 1792379Notes

Reaction equation

HRID 1792379 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH:28][C:29]([O:31][CH3:32])=[O:30])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].O.CCCCCC>CO.O1CCCC1.[Ni].C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:8]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 4311764Sodium borohydrideHCID 54558721HCID 54558721, compound

Product 1

HCID 22033413HCID 22033413, compoundYield 76%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 8-[7-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-yl]-2-octenate (160 mg, 0.34 mmol) in methanol (3 ml) and tetrahydrofuran (1 ml) were added sodium borohydride (129 mg, 3.40 mmol) and nickel (1 ml) chloride hexahydrate (16 mg, 0.068 mmol) at 0° C., which was then stirred at the same temperature for 2 hours. After the reaction was completed, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (118 mg, yield: 73%; (3RS,4RS):(3RS,4SR)=4:1).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product
  5. customThis crude product thus obtained

Sources & evidence

ORD record
ord-4a3eea3c883b434baacd67f68df6e803
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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