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

HRID 709238

Reaction equation

HRID 709238 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][CH2:8][CH:9]1[CH2:12][CH:11]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH2:10]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]1[O:13][CH:11]1[CH2:10][CH:9]([CH2:8][CH2:7][OH:6])[CH2:12]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67249485tert-butyl(diphenyl){2-[3-(tetrahydro-2H-pyran-2-yloxy)cyclobutyl]ethoxy}silane

Product 1

HCID 672483422-[3-(Tetrahydro-2H-pyran-2-yloxy)cyclobutyl]ethanolYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl(diphenyl){2-[3-(tetrahydro-2H-pyran-2-yloxy)cyclobutyl]ethoxy}silane (4.66 g, 10.6 mmol) was dissolved in tetrahydrofuran (50 mL) and tetrabutylammonium fluoride (1.0 N in tetrahydrofuran, 1.66 mL, 10.6 mmol). The reaction was stirred at room temperature overnight. The reaction was evaporated in vacuo and purified on silica gel with a heptane-ethyl acetate gradient (10% ethyl acetate, then 50% ethyl acetate) to give 2-[3-(tetrahydro-2H-pyran-2-yloxy)cyclobutyl]ethanol (2.14 g, 100%) as a yellow oil. Partial 1H NMR indicated a ˜4:1 mix of unknown cis-trans isomers. (CDCl3, δ ppm, key peaks are 4.07 (m, 0.80H), 4.35 (m, 0.20H), 4.54 (m, 0.20H), 4.56 (m, 0.80H).

Workup

  1. customThe reaction was evaporated in vacuo
  2. custompurified on silica gel with a heptane-ethyl acetate gradient (10% ethyl acetate

Sources & evidence

ORD record
ord-2a089137997443cf85dbfb569909af31
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Linked notes

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