Tetrahydrofuran → 3-[(4-Hydroxymethyl-phenyl)-methoxy-methyl]-benzonitrile

HRID 1161074Notes

Reaction equation

HRID 1161074 reaction equation
[CH3:1][O:2][CH:3]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][O:19][Si](C(C)C)(C(C)C)C(C)C)=[CH:14][CH:13]=1)[C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[OH:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([CH:3]([O:2][CH3:1])[C:4]2[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=2)[C:7]#[N:8])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 666995633-[Methoxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile

Product 1

HCID 574383533-[(4-Hydroxymethyl-phenyl)-methoxy-methyl]-benzonitrileYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-[methoxy-(4-triisopropylsilanyloxymethyl-phenyl)-methyl]-benzonitrile (0.4 g, 0.976 mmol), tetrahydrofuran (10 mL) and a 1M tetrahydrofuran solution of tetrabutylammonium fluoride (1.2 mL, 1.2 mmol) is stirred at room temperature 18 hr. The mixture is diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL) and the combined extracts are concentrated. The residue is purified via silica chromatography eluting with hexanes to 1:1 hexanes:ethyl acetate to give the title compound (188 mg, 76%) as a colorless oil. LCMS M+1 254.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. concentrationthe combined extracts are concentrated
  3. customThe residue is purified via silica chromatography
  4. washeluting with hexanes to 1:1 hexanes

Sources & evidence

ORD record
ord-d6505e0ac6bb44fc95738f56b835ed9e
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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