Isopropanol → 2-[6-(Hydroxymethyl)pyridin-2-yl]propan-2-ol

HRID 373759

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[O:12])[CH3:11])[N:5]=1)(=[O:3])C.[BH4-].[Na+].[CH:15](O)(C)C>>[CH3:15][C:10]([CH3:11])([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:1][OH:3])[N:5]=1)[OH:12]

Participants

Reactant 3

HCID 3776Isopropanol

HCID 707902,6-Diacetylpyridine

HCID 4311764Sodium borohydride

Product 1

HCID 191043162-[6-(Hydroxymethyl)pyridin-2-yl]propan-2-ol

Procedure

A 250 mL three-necked round bottom flask fitted with magnetic stirrer and nitrogen inlet was charged with 5.0 g (30.6 mmol) of 2,6-diacetylpyridine and 60 mL of anhydrous isopropyl alcohol. To the stirred solution was added 1.16 g (3.06 mmol) of sodium borohydride in three equal portions. The initially colorless solution became yellow and warmed then slowly returned to pale yellow.

Workup

customA 250 mL three-necked round bottom flask fitted with magnetic stirrer and nitrogen inlet
temperaturewarmed

Sources & evidence

ORD record: ord-5253aa04c36d4454a7238c8a78fabadd
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166062

Linked notes

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