Hydrochloric Acid → HCID 23083167, compound

HRID 2422265Notes

Reaction equation

HRID 2422265 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=1)[CH3:2].[BH4-].[Na+].Cl>CO.O1CCCC1.C(OCC)(=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=1)[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 23082997HCID 23082997, compound

Product 1

HCID 23083167HCID 23083167, compoundYield 80.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2′,6′-diethylbiphenyl-3-carbaldehyde (3.48 g, 14.6 mmol) in a mixture of methanol (35 mL) and tetrahydrofuran (35 mL) was added sodium borohydride (0.28 g, 7.3 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was adjusted to pH 3 with 1N hydrochloric acid, diluted with ethyl acetate, washed successively with water and saturated brine, dried (magnesium sulfate), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give the title compound (2.82 g, yield 80%) as a colorless oil.

Workup

  1. temperaturecooling
  2. washwashed successively with water and saturated brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

Sources & evidence

ORD record
ord-1c6bfd0d95e74b1286943945acc6802d
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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