Hexane → 1-(Methanesulfinyl)-1-(methylsulfanyl)cyclopentane

HRID 329262Notes

Reaction equation

HRID 329262 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]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 178418339Butyllithium

Product 1

HCID 132987881-(Methanesulfinyl)-1-(methylsulfanyl)cyclopentaneYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. customat -16° C.
  2. 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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