Sodium Methoxide → HCID 18594804, compound
Reaction equation
C([S:4][CH:5]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:6][CH2:7][C@@H:8]1[C@@H:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11](=[O:24])[CH2:10][CH2:9]1)(=O)C.C[O-].[Na+]>CO>[O:24]=[C:11]1[CH2:10][CH2:9][C@H:8]([CH2:7][CH2:6][CH:5]([SH:4])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 606 mg. of ethyl 15-acetylthio-9-oxoprostanoate (Example 113) in 20 ml. of reagent methanol is treated, under nitrogen atmosphere, with 1.6 ml. of 1N methanolic sodium methoxide. After 10 minutes the reaction is quenched by the addition of 0.3 ml. of glacial acetic acid and taken to dryness. A solution of the residue in ether is washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to afford 428 mg. (89%) of an oil; λmax. 4.0 (sulfhydryl) and 5.78 μ (carbonyls).