Hexane → 1-(Methanesulfinyl)-1-(methylsulfanyl)cyclopentane
Reaction equation
[CH3:1][S:2][CH2:3][S:4](=[O:6])[CH3:5].[CH3:7][CH2:8][CH2:9][CH2:10]CC.C([Li])CCC>O1CCCC1>[CH3:1][S:2][C:3]1([S:4](=[O:6])[CH3:5])[CH2:10][CH2:9][CH2:8][CH2:7]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Formaldehyde dimethyl mercaptal S-oxide (1.166g) was dissolved in 10 ml. of tetrahydrofuran, and at -16° C., 7.2 ml. of an n-hexane solution (1.4 millimols/milliliter) of n-butyl lithium was added, followed by stirring the mixture for 2.5 hours. 1,4-Bis(methanesulfonato)butane (904 mg) was added together with 35 ml. of tetrahydrofuran. The mixture was stirred for 21 hours at room temperature. Then, the same procedure as in Example A-14 was repeated to afford 465 mg of cyclopentanone dimethyl mercaptal S-oxide in a yield of 71%.
Workup
- customat -16° C.
- stirringThe mixture was stirred for 21 hours at room temperature
Sources & evidence
- ORD record
- ord-fd7ce230aab0443b9617a1678359e271
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04020171
Reaction notes
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