Methyl iodide → Ethyl 9-ethylenedioxy-15-hydroxy-15-methylprostanoate

HRID 1580211Notes

Reaction equation

HRID 1580211 reaction equation
[Mg].[CH3:2]I.[CH2:4]1[CH2:23][O:22][CH:21]2[CH:6]([C@@H:7]([C@@H:19]([CH2:24][CH2:25][C:26](=[O:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:20]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:5]1.[Cl-].[NH4+]>CCOCC.O>[CH2:4]1[CH2:23][O:22][CH:21]2[CH:6]([C@@H:7]([C@@H:19]([CH2:24][CH2:25][C:26]([OH:32])([CH3:2])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:20]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:5]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 68123704Ethyl 9-ethylenedioxy-15-oxo-prostanoate

Product 1

HCID 68124131Ethyl 9-ethylenedioxy-15-hydroxy-15-methylprostanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

To a Grignard solution prepared from 207 mg. of magnesium and 1.3 g. of methyl iodide in 10 ml. of ether under nitrogen atmosphere is added a solution of 1.77 g. of ethyl 9-ethylenedioxy-15-oxo-prostanoate (Example 56) in 10 ml. of ether and the resulting mixture is stirred at room temperature for 18 hours. Saturated ammonium chloride (20 ml.) is added followed by 10 ml. of water and 50 ml. of ether. The ethereal solution is washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 1.77 g. (94%) of viscous oil; λ max. 2.94 (hydroxyl group) and 5.77 μ (carbonyl group).

Workup

  1. customTo a Grignard solution prepared from 207 mg
  2. washThe ethereal solution is washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customto give 1.77 g

Sources & evidence

ORD record
ord-13e4a1c024254d78a2e07b4ad40afe47
Source dataset
uspto-grants-1976_01
Patent number
US03932463

Reaction notes

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