Diethyl Ether → HCID 19916953, compound

HRID 1464749Notes

Reaction equation

HRID 1464749 reaction equation
[H-].[Na+].[CH2:3]([N:5]([CH2:16][C:17]1[CH:22]=[C:21]([CH2:23][OH:24])[CH:20]=[CH:19][N:18]=1)[CH2:6]/[CH:7]=[CH:8]/[C:9]#[C:10][C:11]([O:14][CH3:15])([CH3:13])[CH3:12])[CH3:4].Br[CH2:26]/[CH:27]=[CH:28]/[C:29]1[CH:33]=[CH:32][S:31][CH:30]=1.C(OCC)C>O1CCCC1>[CH2:3]([N:5]([CH2:16][C:17]1[CH:22]=[C:21]([CH2:23][O:24][CH2:26]/[CH:27]=[CH:28]/[C:29]2[CH:33]=[CH:32][S:31][CH:30]=2)[CH:20]=[CH:19][N:18]=1)[CH2:6]/[CH:7]=[CH:8]/[C:9]#[C:10][C:11]([O:14][CH3:15])([CH3:13])[CH3:12])[CH3:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 19916936HCID 19916936, compoundHCID 19917010HCID 19917010, compound

Product 1

HCID 19916953HCID 19916953, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

11.6 mg of 60% oily sodium hydride was suspended in 0.5 ml of tetrahydrofuran at 0 ° C., under a nitrogen atmosphere, and a tetrahydrofuran solution( 2 ml) of 87.5 mg of (E)-N-ethyl-N-(6-methoxy-6-methyl-2-hepten-4-ynyl)-4-hydroxymethyl-2-pyridylmethylamine was added dropwise. The mixture was stirred for 20 minutes, and a tetrahydrofuran solution (1 ml) of 50 mg of (E)-3-bromo-1-(3-thienyl)-1-propene was added dropwise. The mixture was stirred overnight at room temperature, and then ice water and ethyl ether were added. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by medium-pressure liquid chromatography [silica gel column, chloroform→chloroform/methanol=20/1] to give 56 mg (yield 46%) of the captioned compound as a pale yellow oil.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by medium-pressure liquid chromatography [silica gel column, chloroform→chloroform/methanol=20/1]

Sources & evidence

ORD record
ord-82a48b9c059c47a0b7f06934ec125b61
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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