Dimethyl Sulfide → HCID 67025834, compound

HRID 1808288Notes

Reaction equation

HRID 1808288 reaction equation
S(C)[CH3:2].[C:4]1([CH3:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([O-:14])([O-])=O.[K+].[K+].[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>O>[CH:17]1([CH2:21][O:20][CH2:19][CH2:10][C:4]2[CH:9]=[CH:8][C:7]([CH2:11][OH:14])=[CH:6][CH:5]=2)[CH2:18][CH2:2]1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 1140TolueneHCID 8028TetrahydrofuranHCID 11430Potassium Carbonate

Product 1

HCID 67025834HCID 67025834, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution under nitrogen of 410 mg (1.9 mmol) of the compound prepared in Example 1b, in 100 ml of THF, are added 1.024 ml (2 mmol) of BH3.Me2S (2 M solution in toluene). After stirring for two hours at room temperature, 39.5 ml of water, 89.5 ml of toluene and 283 mg (1.1 equivalents) of K2CO3 dissolved in 39.5 ml of water are added. After separation of the phases by settling, the organic phase is recovered and the aqueous phase is extracted with 80 ml of toluene. The combined organic phases are washed with water, dried over Na2SO4 and concentrated under vacuum to give 299 mg of a yellow oil. This oil is taken up in 35 ml of methanol and stirred for one hour at room temperature.

Workup

  1. additionare added
  2. customAfter separation of the phases
  3. customthe organic phase is recovered
  4. extractionthe aqueous phase is extracted with 80 ml of toluene
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9722c987ae1347b394bdb1a8d6be384d
Source dataset
uspto-grants-2013_01
Patent number
US08357721B2

Reaction notes

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