Methanol → 5,8-Dihydro-5,8-epoxynaphtho[2,3-d]-1,3-dioxole

HRID 1837670Notizen

Reaktionsgleichung

[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:11][OH:12].[OH2:13].[C:14]1([CH3:20])C=CC=CC=1>>[O:1]1[CH:5]2[CH:14]=[CH:20][CH:2]1[C:3]1[C:4]2=[CH:10][C:9]2[O:12][CH2:11][O:13][C:8]=2[CH:7]=1

Komponenten

Edukt 5

HCID 178418339Butyllithium

Produkt 1

HCID 147704315,8-Dihydro-5,8-epoxynaphtho[2,3-d]-1,3-dioxoleAusbeute 54 %

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To 3,4-dibromobenzo-1,3-dioxolane (1.54 g, 5.50 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Recrystallization from hexanes gave 25 (560 mg, 54%) as white crystals). Rf=0.47 on silica gel (30% ethyl acetate:hexanes); mp 111-112° C. (Et2O); IR (KBr, cm−1) 2895, 1455, 1292, 1138, 1038, 1014, 848; 1H NMR (400 MHz, CDCl3) δ 7.02 (2H, dd, J=0.9, 0.9 Hz), 6.82 (2H, s), 5.92 (1H, d, J=1.5 Hz), 5.87 (1H, d, J=1.5 Hz), 5.62 (2H, s); 13C NMR (400 MHz, CDCl3) δ 144.3, 143.3, 103.9, 101.1, 82.4. HRMS calcd for C11H8O2 (M+): 188.0473. Found: 188.0463.

Aufarbeitung

temperatureto warm to rt
waitAfter 3 hours
customThe organic layer was separated
extractionthe aqueous layer was extracted three times with Et2O
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customRecrystallization from hexanes

Quellen und Nachweise

ORD-Eintrag: ord-3c2e25d2aaac4dbe99d81f21f27a2670
Quelldatensatz: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06784210B2

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