3,4-dihydro-2H-pyran → tert-butyl(diphenyl){2-[3-(tetrahydro-2H-pyran-2-yloxy)cyclobutyl]ethoxy}silane

HRID 1183963

Reaktionsgleichung

Reaktionsgleichung von HRID 1183963
[Si:1]([O:18][CH2:19][CH2:20][CH:21]1[CH2:24][CH:23]([OH:25])[CH2:22]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1.N1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1>[C:14]([Si:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[O:18][CH2:19][CH2:20][CH:21]1[CH2:24][CH:23]([O:25][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][O:26]2)[CH2:22]1)([CH3:17])([CH3:15])[CH3:16]

Komponenten

5

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 575657453-(2-{[Tert-butyl(diphenyl)silyl]oxy}ethyl)cyclobutanol

Produkt 1

HCID 67249485tert-butyl(diphenyl){2-[3-(tetrahydro-2H-pyran-2-yloxy)cyclobutyl]ethoxy}silaneAusbeute 105 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-(2-{[Tert-butyl(diphenyl)silyl]oxy}ethyl)cyclobutanol (3.58 g, 10.1 mmol) was dissolved in dry tetrahydrofuran (50 mL) and 2,3-dihydro-4H-pyran and 4-toluenesulfonic acid pyridine salt were added and the reaction was stirred at room temperature for 48 hours. The reaction was concentrated in vacuo and purified on silica gel with a heptane-ethyl acetate gradient (5% ethyl acetate, then 20% ethyl acetate) to give crude tert-butyl(diphenyl){2-[3-(tetrahydro-2H-pyran-2-yloxy)cyclobutyl]ethoxy}silane (4.66 g, 105%) as a milky oil. Partial 1H NMR indicated a ˜4:1 mix of unknown cis-trans isomers. (CDCl3, δ ppm, key peaks are 4.05 (m, 0.80H), 4.30 (m, 0.20H), 4.52 (m, 0.20H), 4.56 (m, 0.80H).

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified on silica gel with a heptane-ethyl acetate gradient (5% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cf6f1f5e42a8442eb2f352eb51319b3d
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664401B2

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