Reaktion #165699

Reaktionsgleichung

NaH

cis-3-benzyloxymethylcyclobutanol

NaH

iodomethane

iodomethane

→

title compound

cis-3-benzyloxymethylcyclobutanol methyl ether

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 16 hours
2. 2
   workup.ADDITIONwere added
3. 3
   workup.STIRRINGthe mixture stirred for an additional 2 hours
4. 4
   SonstigeThe mixture was quenched with 10 mL of NH4Cl
5. 5
   workup.ADDITIONdiluted with 10 mL of ethyl acetate
6. 6
   SonstigeThe layers were separated
7. 7
   Extraktionthe aqueous layer was extracted twice with 5 mL portions of ethyl acetate
8. 8
   TrocknenThe combined organic extracts were dried over anhydrous Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigePurification via column chromatography (SiO2, 75% hexanes in ethyl acetate)

Vorschrift

To a solution of cis-3-benzyloxymethylcyclobutanol (Albany Molecular Research Institute, 1.0 g, 5.2 mmol) in 10 mL of tetrahydrofuran at 0° C. was added NaH (0.62 g, 15.6 mmol). The mixture stirred for 15 minutes and iodomethane (0.49 mL, 7.8 mmol) was added and the mixture was allowed to warm to ambient temperature and stirred for 16 hours. Some starting material remained by TLC so additional NaH (0.21, 5.2 mmol) and iodomethane (0.32 mL, 5.2 mmol) were added and the mixture stirred for an additional 2 hours. The mixture was quenched with 10 mL of NH4Cl and diluted with 10 mL of ethyl acetate. The layers were separated and the aqueous layer was extracted twice with 5 mL portions of ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 75% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 207 (M+H)+.

Quelle