4-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile → 4-(Hydroxymethyl)pyridine-2-carbonitrile

HRID 619854Notes

Reaction equation

HRID 619854 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][O:10][Si](C(C)(C)C)(C)C)[CH:6]=[CH:5][N:4]=1)#[N:2]>CO>[C:1]([C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][N:4]=1)#[N:2]

Participants

3

Reactant 1

HCID 145414484-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile

Product 1

HCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrileYield 88.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-cyano-4-[{(tert-butyldimethylsilyl)oxy}methyl]pyridine (10.1 g, 40.5 mmol) in 200 mL of anhydrous MeOH is stirred over 12 g of Dowex-50W-H+ ion-exchange resin (pre-washed with MeOH) for a period of 18 hours. After this time, the mixture is filtered and washed with MeOH twice. The combined filtrates are concentrated in vacuo. The crude residue is purified by column chromatography eluting with 50% EtOAc/hexanes to afford the title compound (4.82 g, 35.9 mmol) as an oil.

Workup

  1. filtrationAfter this time, the mixture is filtered
  2. washwashed with MeOH twice
  3. concentrationThe combined filtrates are concentrated in vacuo
  4. customThe crude residue is purified by column chromatography
  5. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-8ebb08e77ea5415f85f415091f43055b
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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