Tetrabutylammonium Fluoride → 2-Fluoro-5-[(4-hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

HRID 1161049Notes

Reaction equation

HRID 1161049 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([SiH2][O:24][C:25](C)(C)[C:26]1[CH:31]=[CH:30][C:29]([CH:32]([O:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][O:44]2)[C:33]2[CH:34]=[CH:35][C:36]([F:41])=[C:37]([CH:40]=2)[C:38]#[N:39])=[CH:28][CH:27]=1)(C)(C)C>ClCCl>[F:41][C:36]1[CH:35]=[CH:34][C:33]([CH:32]([C:29]2[CH:28]=[CH:27][C:26]([CH2:25][OH:24])=[CH:31][CH:30]=2)[O:42][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][O:44]2)=[CH:40][C:37]=1[C:38]#[N:39]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1373294185-[[4-(Tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-2-fluoro-benzonitrile

Product 1

HCID 666995842-Fluoro-5-[(4-hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add tetrabutylammonium fluoride (1.0M in tetrahydrofuran, 5.27 mL, 5.27 mmol) to 5-[[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-2-fluoro-benzonitrile (1.20 g, 2.64 mmol) and stir the solution overnight. Dilute with dichloromethane and wash with water and brine. Dry the organic layer and concentrate the solution to afford the title compound (0.890 g, 2.60 mmol, 99%, mixture of diastereomers): 1H NMR (400 MHz, CDCl3) δ 1.55 (m, 2H), 1.68 (m, 2H), 1.74 (m, 2H), 3.46 (m, 1H), 3.77 (m, 1H), 4.60 (m, 1H), 4.67 (s, 2H), 5.78 (s, 1H), 7.10 (m, 1H), 7.27 (m, 4H), 7.55 (m, 1H), 7.64 (m, 1H).

Workup

  1. washwash with water and brine
  2. customDry the organic layer
  3. concentrationconcentrate the solution

Sources & evidence

ORD record
ord-19d10f48ac3b477c8fe342ff1e60c03f
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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