Citric Acid → HCID 67265323, compound

HRID 1685802Notes

Reaction equation

HRID 1685802 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][S:4][C:3]1=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][S:4][C:3]1=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 67265411HCID 67265411, compound

Product 1

HCID 67265323HCID 67265323, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[4-(3-Oxothian-2-ylidenemethyl)phenyl]propionic acid (80 mg) obtained in Example 4 was dissolved in methanol (1.0 ml), and to the solution was added sodium borohydride (11 mg) under ice cooling. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was acidified with 10% aqueous citric acid, and extracted with chloroform. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (24 mg, 30%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e1bef131b2e743299b3c66d59a437e5a
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

Loading…