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

HRID 328516Notes

Reaction equation

HRID 328516 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-0024128f7db944d182b0b1ef62a51cda
Source dataset
uspto-grants-1977_04
Patent number
US04017534

Reaction notes

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