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

HRID 1717736Notes

Reaction equation

HRID 1717736 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-92c30ba63f664860ac590884097b960c
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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