3,4-dihydro-2H-pyran → 2-(5-Bromo-2-methyl-2-phenylpentyloxy)-tetrahydropyran

HRID 969046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 969046
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:6][OH:7].[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:6][O:7][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:15]1

Komponenten

5

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 113458925-Bromo-2-methyl-2-phenylpentan-1-ol

Produkt 1

HCID 114846082-(5-Bromo-2-methyl-2-phenylpentyloxy)-tetrahydropyranAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

According to the method described for the synthesis of 207d, 206b (20.0 g, 77.8 mmol) was treated with 3,4-dihydro-2H-pyran (8.2 g, 96.5 mmol) and p-toluenesulfonic acid hydrate (0.57 g, 3.0 mmol) in CH2Cl2 (350 mL) to afford 207b (25.2 g, 95%) as an oil, which was used without further purification. 1H NMR (CDCl3): 7.26-7.08 (m, 5H), 4.45 (m, 1H), 3.72 (m, 1H), 3.58 (m, 1H), 3.35-3.05 (m, 2H), 3.28 (t, 2H, J=6.6), 1.95-1.39 (m, 10H), 1.25 (s, 3H). 13C NMR (CDCl3): δ 145.38, 128.15, 126.51, 126.03, 99.06, 98.92, 76.20, 61.91, 61.80, 41.82, 41.74, 37.58, 37.43, 34.65, 30.61, 27.88, 25.58, 23.03, 22.90, 19.39, 19.32. HRMS (LSIMS, nba): Calcd for C17H26O2Br (MH+): 341.1116, found: 341.1127.

Quellen und Nachweise

ORD-Eintrag
ord-178c59e6ea72481baeaaef594db1b036
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304093B2

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