Water → 3-(Benzyloxy)cyclobutan-1-one

温度

-20 °C

Methylsulfinyl(methylthio)methane (13 ml, 125 mmol) was dissolved in 250 ml THF and cooled to −20° C. n-Butyllithium (50 ml, 125 mmol) was added and the mixture was stirred for 3 h at −20° C. The mixture was cooled down to −78° C. and a solution of 1-((1,3-dibromopropan-2-yloxy)methyl)benzene (16.000 g, 52 mmol) was added. The reaction was stirred over night and allowed to warm up to RT. It was stirred for an additional 6 h at RT, hydrolyzed with water and extracted with EtOAc. The combined organic extracts were evaporated, dissolved in ether (50 ml) and treated with conc. HCl (10 ml) for 30 min at reflux. The mixture was neutralized with NaOH (10M) and extracted with EtOAc. The combined organic extracts were dried over MgSO4 and evaporated. Glass col. Chrom. (10-50% EtOAc in Hex) gave 3-(benzyloxy)cyclobutanone as a yellow oil.

1. additionwas added
2. temperatureThe mixture was cooled down to −78° C.
3. stirringThe reaction was stirred over night
4. temperatureto warm up to RT
5. extractionextracted with EtOAc
6. customThe combined organic extracts were evaporated
7. dissolutiondissolved in ether (50 ml)
8. additiontreated with conc. HCl (10 ml) for 30 min
9. temperatureat reflux
10. extractionextracted with EtOAc
11. dry with materialThe combined organic extracts were dried over MgSO4
12. customevaporated

ORDレコード

ord-62640e8f36fa48219755166f11fe779e

出典データセット

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07973047B2