S-Methyl methanethiosulfonate → HCID 19602330, compound

HRID 1604239Notes

Reaction equation

HRID 1604239 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:7]2[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=2[S:9][C:10]=1[Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:5])[CH3:2].[Li]CCCC.[CH3:24][S:25]S(C)(=O)=O>C1COCC1.CCCCCC>[CH2:1]([N:3]([S:25][CH3:24])[C:4]([C:6]1[C:7]2[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=2[S:9][C:10]=1[Si:11]([CH3:12])([CH3:13])[CH3:14])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 18064S-Methyl methanethiosulfonateHCID 19602331HCID 19602331, compoundHCID 178418339Butyllithium

Product 1

HCID 19602330HCID 19602330, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of the product of Example 8 (1.1 g, 4 mmol) in 20 mL THF at <-60° C. under a positive nitrogen atmosphere was added dropwise 2.5M of n-BuLi in hexane (2.2 mL) at <-60° C., and the solution was stirred for 0.5 h. A solution of methyl methanethiolsulfonate (0.6 g, 4.8 mmol) in 2 mL THF was added at <-60° C. After 1 h at ambient temperature, the solution was poured into ice water and extracted with methylene chloride. The organic layer was washed with brine, dried, and concentrated in vacuo. The residue was purified on a silica gel column using 8% ethyl acetate-hexane to give 1 g of the desired product as a viscous yellow oil, a yield of 76.9%. nD24 1.5886.

Workup

  1. waitAfter 1 h at ambient temperature
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-651c8e4b69e54862a69ff653f5f257bc
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

Loading…