Water → HCID 22234986, compound

HRID 749611Notes

Reaction equation

HRID 749611 reaction equation
[BH4-].[Na+].[CH:3]([CH2:5][CH2:6][C:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)([C:10]#[N:11])[C:8]#[N:9])=[O:4].O>C(O)C>[OH:4][CH2:3][CH2:5][CH2:6][C:7]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=1)([C:10]#[N:11])[C:8]#[N:9]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22235036HCID 22235036, compound

Product 1

HCID 22234986HCID 22234986, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 0.01 g of sodium borohydride was added to the solution of 0.30 g of 2-(2-formylethyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (the intermediate (19)) in ethanol at 0° C., followed by stirring for 5 hours at room temperature. Then, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.19 g of 2-(3-hydroxypropyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (the intermediate (20)).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8cb2e486f3b34fe591375a0bb1a505e3
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

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