Methyl iodide → Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate

HRID 574950

Reaktionsgleichung

[CH:1](NC(C)C)(C)C.[Li]CCCC.[O:13]1[C:17]2([CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1.CI>O1CCCC1.O>[CH3:1][C:20]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:22][C:17]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:18][CH2:19]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Into a 500 mL round-bottomed flask was added diisopropylamine (7.98 mL) in tetrahydrofuran (233 mL) to give a colorless solution. The mixture was cooled to −78° C. under N2 and n-BuLi (2.5 M in hexanes, 22.40 mL) was added. The reaction was stirred for 30 minutes and ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (10 g) was added. The reaction was allowed to stir for 1.5 hours upon which time CH3I (4.38 mL) was added. The reaction was allowed to warm to room temperature overnight with stirring. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organics were dried (Na2SO4), filtered and concentrated by rotary evaporation. The residue was purified by normal phase flash column chromatography (Analogix, 0-50% hexanes/ethyl acetate).

Aufarbeitung

customto give a colorless solution
additionwas added
temperatureto warm to room temperature overnight
stirringwith stirring
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialThe combined organics were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated by rotary evaporation
customThe residue was purified by normal phase flash column chromatography (Analogix, 0-50% hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-db027b31eeec4e5c99c853a29ea59b36
Quelldatensatz: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09034875B2

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