Methyl iodide → HCID 11171949, compound

HRID 1165030Notes

Reaction equation

HRID 1165030 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[O:16][Si](C(C)(C)C)(C)C)[CH:4]=[CH2:5].CI.C(Cl)Cl.[O:29]1CCC[CH2:30]1>CO.Cl>[CH3:30][O:29][CH2:5][CH2:4][CH2:3][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[OH:16]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 15617924HCID 15617924, compound

Product 1

HCID 11171949HCID 11171949, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent

Procedure

A suspension of sodium hydride (60% in mineral oil; 0.28 g, 0.007 mole) in dry tetrahydrofuran (5 mL) was stirred at 0°. A solution of the product of Example 122 Part B (2.00 g, 0.006 mole) was added slowly, and the mixture warmed to room temperature. Methyl iodide (0.8 mL, 0.013 mole) was added, the mixture was stirred for 3 hours, then was poured into 1.0N hydrochloric acid. The crude material was isolated by extraction with methylene chloride, dissolved in a mixture of methanol (20 mL) and 1.0N hydrochloric acid (20 mL), and heated at reflux for 20 hours. The cooled solution was extracted with methylene chloride, and the residue was chromatographed with 9:1 petroleum ether/ether to provide the title compound (0.90 g, 66%) as a colorless oil. Mass spectrum: m/z 216.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. temperatureheated
  3. temperatureat reflux for 20 hours
  4. extractionThe cooled solution was extracted with methylene chloride
  5. customthe residue was chromatographed with 9:1 petroleum ether/ether

Sources & evidence

ORD record
ord-fb1f9ca968bf49d399f4fd58357ea5e2
Source dataset
uspto-grants-1990_03
Patent number
US04906636

Reaction notes

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