Water → 3-(6-Chloropyridin-3-yl)-2-methylpropan-1-ol

HRID 1714418Notes

Reaction equation

HRID 1714418 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:13])[C:10](O)=[O:11])=[CH:4][CH:3]=1.B.O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:13])[CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 14798Sodium HydroxideHCID 540894253-(6-Chloropyridin-3-yl)-2-methylpropanoic acid

Product 1

HCID 592152003-(6-Chloropyridin-3-yl)-2-methylpropan-1-olYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-(6-chloropyridin-3-yl)-2-methylpropanoic acid (6.5 g, 32.6 mmol) in THF (75 mL) cooled in an ice-water bath was added a solution of 1 M borane in THF (48 mL, 48 mmol) in a rapid dropwise fashion. The mixture was stirred at room temperature for 4 h. Water (25 mL) was added carefully followed by 2 N NaOH solution. The two phases were separated and the aqueous phase washed with ether (100 mL). The organic phases were combined, dried over anhydrous MgSO4, filtered, and concentrated to give 4.2 g of the product as a nearly colorless oil in 69% crude yield. [M+H]+=186, 188; IR: 3414 (OH)

Workup

  1. customThe two phases were separated
  2. washthe aqueous phase washed with ether (100 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b71bffad76da4819abd4883abf6dc121
Source dataset
uspto-grants-2010_09
Patent number
US07795456B2

Reaction notes

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