Sodium Methoxide → HCID 18594804, compound

HRID 1580235Notes

Reaction equation

HRID 1580235 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; λmax. 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-9b63541ab430480fb40b028b798140fe
Source dataset
uspto-grants-1976_01
Patent number
US03932472

Reaction notes

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