Reaction equation
CS(CSC)=O.[CH2:7]([O:14][CH:15]1[CH2:18][C:17](=[O:19])[CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([Li])CCC.BrCC(OCC1C=CC=CC=1)CBr.O>C1COCC1>[CH2:7]([O:14][CH:15]1[CH2:18][C:17](=[O:19])[CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
Conditions
- Temperature
- -20 °C
Procedure
3-(Benzyloxy)cyclobutanone 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 6h 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.
Workup
- additionwas added
- temperatureThe mixture was cooled down to −78° C.
- stirringThe reaction was stirred over night
- temperatureto warm up to RT
- extractionextracted with EtOAc
- customThe combined organic extracts were evaporated
- dissolutiondissolved in ether (50 ml)
- additiontreated with conc. HCl (10 ml) for 30 min
- temperatureat reflux
- extractionextracted with EtOAc
- dry with materialThe combined organic extracts were dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-209392541b7d4708aa42d3647a0d987d
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745484B2
Linked notes
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