Citric Acid → HCID 58903178, compound

HRID 273371Notes

Reaction equation

HRID 273371 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C2CCCCO2)[CH:5]=[C:4]([CH3:15])[C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[O:23])[CH:17]=1.[BH4-].[Na+].[C:26]([OH:38])(=O)[CH2:27][C:28]([CH2:33][C:34](O)=O)(C(O)=O)O>COCCOC.O1CCCC1>[CH3:15][C:4]1[CH:5]=[C:6]([OH:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][CH:26]2[CH2:27][CH2:28][CH2:33][CH2:34][O:38]2)[CH:17]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 58903143HCID 58903143, compound

Product 1

HCID 58903178HCID 58903178, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2′,6′-Dimethyl-4′-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-carbaldehyde (9.05 g, 29.2 mmol) was dissolved in a mixture of 1,2-dimethoxyethane (50 mL) and tetrahydrofuran (50 mL), and sodium borohydride (0.567 g, 15.0 mmol) was added under ice-cooling. The mixture was stirred at the same temperature for 3 hrs. 10% Aqueous citric acid solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15%-50% ethyl acetate/hexane) to give the title compound (3.24 g, yield 36%) as colorless crystals.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (15%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d98125142a5a4a84a5282ffd321d7208
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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