Tetrabutylammonium Fluoride → [3-(Tetrahydro-pyran-2-yloxy)-cyclobutyl]-methanol

HRID 1907317Notes

Reaction equation

HRID 1907317 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH:8]1[CH2:11][CH:10]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH2:9]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.ClCCl>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]1[O:12][CH:10]1[CH2:9][CH:8]([CH2:7][OH:6])[CH2:11]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66779971HCID 66779971, compound

Product 1

HCID 66779483[3-(Tetrahydro-pyran-2-yloxy)-cyclobutyl]-methanolYield 83.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl dimethyl-[3-(tetrahydropyran-2-yloxy)-cyclobutylmethoxy]-silane (1.62 g) was dissolved in tetrahydrofuran (11 mL) and treated with a solution of 1.0M tetrabutylammonium fluoride in tetrahydrofuran (8.08 mL) for 2 hours. The reaction mixture was diluted with dichloromethane and the mixture was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate in cyclohexane (0 to 2:3 by volume) to give the title compound (0.84 g). 1H NMR (300 MHz, CHCl3-d): δ 4.62-4.54 (m, 1H), 4.29-4.20 (m, 1H), 3.88 (d, 1H), 3.68-3.60 (m, 2H), 3.53-3.42 (m, 1H), 2.30-2.20 (m, 2H), 2.19-2.08 (m, 2H), 1.86-1.72 (m, 3H), 1.58-1.47 (m, 4H), 1.34 (s, 1H).

Workup

  1. washthe mixture was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with ethyl acetate in cyclohexane (0 to 2:3 by volume)

Sources & evidence

ORD record
ord-9b40a640e5bf4132971b6948c8fe1554
Source dataset
uspto-grants-2013_12
Patent number
US08598154B2

Reaction notes

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