Ammonium Chloride → [2'-methyl-4'-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-yl]methanol

HRID 273369Notes

Reaction equation

HRID 273369 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[O:22])[CH:16]=1.[BH4-].[Na+].[Cl-].[NH4+]>COCCOC.O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][OH:22])[CH:16]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 231118322'-methyl-4'-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-carbaldehyde

Product 1

HCID 23111813[2'-methyl-4'-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-yl]methanolYield 89.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2′-Methyl-4′-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-carbaldehyde (13.6 g, 45.9 mmol) was dissolved in a mixture of 1,2-dimethoxyethane (70 mL) and tetrahydrofuran (70 mL), and sodium borohydride (0.870 g, 23.0 mmol) was added under ice-cooling. The mixture was stirred at the same temperature for 3 hrs. To the reaction mixture was added aqueous ammonium chloride solution, 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 (12.2 g, yield 89%) as a colorless oil.

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-c4d2eec61af5450ea2d407384792b530
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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