Water → HCID 19390138, compound

HRID 1757261Notes

Reaction equation

HRID 1757261 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][CH:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[CH:30]=[CH:29][S:28][CH:27]=3)[CH:21]=2)[CH:13]=1)[CH2:9][OH:10].[CH3:33]I.[H-].[Na+].O>CN(C)C=O.C(OCC)C>[CH3:33][O:10][CH2:9][CH:8]([CH2:7]/[CH:6]=[CH:5]/[C:4]#[C:3][C:2]([CH3:32])([CH3:31])[CH3:1])[CH2:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][CH2:19][C:20]1[CH:21]=[C:22]([C:26]2[CH:30]=[CH:29][S:28][CH:27]=2)[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15288603HCID 15288603, compound

Product 1

HCID 19390138HCID 19390138, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

44.4 mg of (E)-2-(6,6-dimethyl-2-hepten-4-ynyl)-3-[3-[3-(3-thienyl)phenylmethoxy]phenyl]propanol obtained in Example 11 is dissolved in 1 ml of dimethylformamide, 17.4 μl of methyl iodide and 8 mg of 60% oily sodium hydride are added under ice cooling and stirring, and the mixture is stirred at room temperature for 4 hours. Water and ethyl ether are added to the reaction solution for dilution, and the organic layer is taken, washed with saturated saline and dried over anhydrous magnesium sulfate. The desiccating agent is filtered, the solvent is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography [Wako gel C-200, 7 g; hexane/ethyl acetate=19/1] to obtain 39 mg (yield: 80%) of the captioned compound as a colorless oily matter.

Workup

  1. stirringthe mixture is stirred at room temperature for 4 hours
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent is filtered
  5. distillationthe solvent is distilled off under reduced pressure
  6. customthe residue is purified by silica gel column chromatography [Wako gel C-200, 7 g; hexane/ethyl acetate=19/1]

Sources & evidence

ORD record
ord-36cfbc3fe610492c95d8c1d936933c11
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

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