Methyl iodide → HCID 70590377, compound

HRID 1679385Notes

Reaction equation

HRID 1679385 reaction equation
[OH:1][CH:2]1[CH2:15][CH:14]([OH:16])[C@H:13]([S:17][CH2:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C@H:3]1[CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[CH3:26][Mg]I.[Mg].CI>C(OCC)C>[OH:1][CH:2]1[CH2:15][CH:14]([OH:16])[C@H:13]([S:17][CH2:18][C:19]([OH:25])([CH3:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C@H:3]1[CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 70589775HCID 70589775, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 70590377HCID 70590377, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Add dropwise 0.37 g. 9,11-dihydroxy-15-oxo-13-thia-5-prostenoic acid, dissolved in 10 ml. dry diethyl ether, to a methyl magnesium iodide solution, prepared from 0.024 g. magnesium shavings and 0.14 g. methyl iodide in 15 ml. dry diethyl ether, stir the reaction for one hour, pour into 50 ml. saturated aqueous NH4Cl solution, extract with diethyl ether, dry the organic phase over Na2SO4 and distill off the solvent to obtain, as the residue, 9,11,15-trihydroxy-15-methyl-13-thia-5-prostenoic acid.

Workup

  1. additionAdd dropwise 0.37 g
  2. customthe reaction for one hour
  3. additionpour into 50 ml
  4. extractionsaturated aqueous NH4Cl solution, extract with diethyl ether
  5. dry with materialdry the organic phase over Na2SO4
  6. distillationdistill off the solvent

Sources & evidence

ORD record
ord-83a20fe6921444c2ac672c1b704e4b24
Source dataset
uspto-grants-1978_03
Patent number
US04080458

Reaction notes

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