Water → Methyl 2'-cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

HRID 1845301Notes

Reaction equation

HRID 1845301 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]([C:20](OC)=[O:21])[CH:11]=1)#[N:2].[BH4-].[Na+].O>CO>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:11]=[C:12]([CH2:20][OH:21])[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:15]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58188054Dimethyl 2'-cyano-4'-methylbiphenyl-3,5-dicarboxylate

Product 1

HCID 58187956Methyl 2'-cyano-5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of dimethyl 2′-cyano-4′-methylbiphenyl-3,5-dicarboxylate (343 mg, 1.05 mmol) in methanol (20 mL) was cooled at 0° C. and sodium tetrahydroborate (0.60 g, 16 mmol) was added slowly. The mixture was stirred at rt for 6 h, and then treated with water (20 mL). The volatiles were removed in vacuo and the acqueous phase was extracted with CH2Cl2 (30 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound.

Workup

  1. customThe volatiles were removed in vacuo
  2. extractionthe acqueous phase was extracted with CH2Cl2 (30 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ba76b2e10c644971818b87d6f703e7f2
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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