Methyl iodide → HCID 54386275, compound

HRID 1637107Notes

Reaction equation

HRID 1637107 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:19]#[C:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:17][OH:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CI.[CH3:31]OS(OC)(=O)=O>C(COC)OC.CN(C=O)C>[CH3:31][O:18][CH2:17][CH2:16][CH:15]([C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1)[C:19]#[C:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 54396505HCID 54396505, compound

Product 1

HCID 54386275HCID 54386275, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-phenylpent-4-ynol (175 mg, 0.5 mmol) in a mixture of glyme (7 ml) and DMF (2 ml) was treated with NaH (20 mg of a 60% dispersion in mineral oil), heated to 50° for 3 min, and cooled to 23°. MeI (0.5 ml) was added, and the mixture stirred for 18 hr. Me2SO4 (0.3 ml) was added, and the mixture was heated to 60° for 2 hr. The reaction was cooled, quenched with 50 ml cold 0.1N HCl, and extracted with Et2O. The extracts were washed with H2O, dried, and the solvent evaporated. Purification by flash chromatography (silica gel, 30% EtOAc in hexane) gave the titled compound, (26 mg 14%). 1H NMR (400 MHz, CDCl3) δ 7.42 (m, 2 H), 7.28 (m, 3 H), 6.96 (m, 2 H), 6.82 (d, 1 H), 4.80 (m, 1 H), 3.98 (t, 1 H), 3.84 (s, 3 H), 3.62 (m, 1 H), 3.48 (m, 1 H), 3.40 (s, 3 H), 2.06 (m, 2 H), 1.72-2.00 (m, 6 H), 1.62 (m, 2 H).

Workup

  1. temperatureheated to 50° for 3 min
  2. temperaturecooled to 23°
  3. temperaturethe mixture was heated to 60° for 2 hr
  4. temperatureThe reaction was cooled
  5. customquenched with 50 ml cold 0.1N HCl
  6. extractionextracted with Et2O
  7. washThe extracts were washed with H2O
  8. customdried
  9. customthe solvent evaporated
  10. customPurification by flash chromatography (silica gel, 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-2e425ecf2fbb44ee822991fdb9b90602
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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