Water → HCID 58127942, compound

HRID 1257360Notes

Reaction equation

HRID 1257360 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:9]2[S:13][C:12]([C:14](OCC)=[O:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].O>O1CCCC1.C(O)C>[F:19][C:2]([F:1])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[S:13][C:12]([CH2:14][OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 46912004HCID 46912004, compound

Product 1

HCID 58127942HCID 58127942, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a mixed solution of the compound (2.5 g, 8.0 mmol) obtained in Example 39a in tetrahydrofuran/ethanol (v/v=1/2, 36 mL) were added sodium tetrahydroborate (1.8 g, 48 mmol) and calcium chloride (5.4 g, 48 mmol), and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude title compound (1.4 g, 68%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9f8a9684051549e6807d742796279b62
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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