Sodium methanethiolate → HCID 18701932, compound

HRID 2289092Notes

Reaction equation

HRID 2289092 reaction equation
Cl[C:2]1[C:9]([CH2:10][CH2:11][CH3:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:21][S-:22].[Na+]>CN(C=O)C>[CH3:21][S:22][C:2]1[C:9]([CH2:10][CH2:11][CH3:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 18702004HCID 18702004, compound

Product 1

HCID 18701932HCID 18701932, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-chloro-3-propyl-4-benzyloxybenzaldehyde (Step C; 0.683 grams) in dry DMF (7 mL) was treated with sodium methanethiolate (0.166 grams). The solution was stirred at 50° C. for 3 hours. The reaction mixture was partitioned between isopropyl acetate and pH 7 buffer. The organic was washed 3 times with water, then dried over magnesium sulfate. Filtration and concentration afforded an oil which was chromatographed over silica gel to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between isopropyl acetate and pH 7 buffer
  2. washThe organic was washed 3 times with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration
  5. customafforded an oil which
  6. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-60bee68448cd4fd2abdbb4d9d3e32fb4
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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