Methyl iodide → HCID 86748930, compound

HRID 1757259Notes

Reaction equation

HRID 1757259 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH:4]([CH2:23]/[CH:24]=[CH:25]/[C:26]#[C:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:5](=[O:22])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[CH:12]=1.CI.[H-].[Na+].[C:37](OCC)(=O)C>O1CCCC1.O.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:32])[C:4]([CH3:37])([CH2:23]/[CH:24]=[CH:25]/[C:26]#[C:27][C:28]([CH3:29])([CH3:31])[CH3:30])[C:5](=[O:22])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[CH:12]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86748931HCID 86748931, compound

Product 1

HCID 86748930HCID 86748930, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

750 mg of (E)-2-(6,6-dimethyl-2-hepten-4-ynyl)-7-[3-(3-thienyl)phenoxy]-3-oxoheptanoic acid methyl ester is dissolved in 10 ml of tetrahydrofuran, 0.16 ml of methyl iodide and 85 mg of 60% oily sodium hydride are added under ice cooling and stirring, and the mixture is stirred for 3 hours under ice cooling. The reaction solution is diluted with water, acetic acid is added for neutralization to pH 7, extraction is made with ethyl acetate, the extract is washed with saturated saline and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography [Wako gel C-200, 30 g; hexane/ethyl acetate=6/1] to obtain 705 mg (yield: 92%) of (E)-2-methyl-2-(6,6-dimethyl-2-hepten-4-ynyl)-7-[3-(3-thienyl)phenoxy]-3-oxoheptanoic acid methyl ester as colorless oil.

Workup

  1. stirringthe mixture is stirred for 3 hours under ice cooling
  2. additionis added for neutralization to pH 7, extraction
  3. washthe extract is washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by silica gel column chromatography [Wako gel C-200, 30 g; hexane/ethyl acetate=6/1]

Sources & evidence

ORD record
ord-ff62789684c7449eac23e300eb439e0d
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

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