Sodium Methoxide → HCID 18594804, compound

HRID 2071343Notes

Reaction equation

HRID 2071343 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

HCID 10942334Sodium MethoxideHCID 18594874HCID 18594874, compound

Product 1

HCID 18594804HCID 18594804, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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; λ max. 4.0 (sulfhydryl) and 5.78 μ (carbonyls).

Workup

  1. customAfter 10 minutes the reaction is quenched by the addition of 0.3 ml
  2. washA solution of the residue in ether is washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customto afford 428 mg

Sources & evidence

ORD record
ord-d501d568d263435799c2eedc70bd2be2
Source dataset
uspto-grants-1977_09
Patent number
US04046787

Reaction notes

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