2-[5-(Tert-butyldimethylsiloxymethyl)pyridin-2-yl]benzonitrile → 2-(5-(Hydroxymethyl)pyridin-2-yl)benzonitrile

HRID 1886071Notes

Reaction equation

HRID 1886071 reaction equation
[O:1]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]#[N:19])=[N:14][CH:15]=1)[Si](C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O>C1COCC1.CCOC(C)=O>[OH:1][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]#[N:19])=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 99963952-[5-(Tert-butyldimethylsiloxymethyl)pyridin-2-yl]benzonitrileHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrate

Product 1

HCID 100360172-(5-(Hydroxymethyl)pyridin-2-yl)benzonitrileYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[5-(tert-butyldimethylsiloxymethyl)pyridin-2-yl]benzonitrile (4.9 g, 0.021 mol) and nBu4NF hydrate (8.1 g, 0.031 mol) in THF (60 mL) was stirred at room temperature for 18 h. The mixture was diluted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated to give 3.5 g (80%) of product as a brown solid, mp 152°-153° C.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e768228e33324aa4bed0f870bda29dc3
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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