Tetrabutylammonium Fluoride → 3-Hydroxymethyl-5-methoxymethyl-benzonitrile

HRID 1167338Notes

Reaction equation

HRID 1167338 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([CH2:16][O:17][CH3:18])[CH:15]=1)[C:11]#[N:12])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([CH2:16][O:17][CH3:18])[CH:15]=1)[C:11]#[N:12]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1373287443-(Tert-butyl-dimethyl-silanyloxymethyl)-5-methoxymethyl-benzonitrile

Product 1

HCID 229962313-Hydroxymethyl-5-methoxymethyl-benzonitrileYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(tert-butyl-dimethyl-silanyloxymethyl)-5-methoxymethyl-benzonitrile (1.402 g, 4.810 mmol) in tetrahydrofuran (10 mL) at room temperature was added tetrabutylammonium fluoride (5.051 mL, 5.051 mmol, 1 M in tetrahydrofuran). The reaction mixture was stirred at room temperature for 2 h then concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 40% ethyl acetate in hexanes yielded 3-hydroxymethyl-5-methoxymethyl-benzonitrile (713 mg, 84%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customPurification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  3. washeluting with 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-eb81b3a6fd434475a1a59db0f2e30ac0
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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