3-Chloro-2-methyl-1-propene → HCID 137226532, compound

HRID 1900834Notes

Reaction equation

HRID 1900834 reaction equation
[OH:1][C:2]1[C:3]2[C:8]([C:9]([CH3:12])=[CH:10][CH:11]=1)=[N:7][C:6](=[O:13])[C:5]([CH3:15])([CH3:14])[CH:4]=2.Cl[CH2:17][C:18]([CH3:20])=[CH2:19].C(=O)([O-])[O-].[K+].[K+]>CCOCC>[CH3:19][C:18](=[CH2:17])[CH2:20][C:11]1[CH:10]=[C:9]([CH3:12])[C:8]2[C:3](=[CH:4][C:5]([CH3:15])([CH3:14])[C:6](=[O:13])[N:7]=2)[C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 137226530HCID 137226530, compound

Product 1

HCID 137226532HCID 137226532, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using 5-hydroxy-3,3,8-trimethylcarbostyril (1.99 g, 9.69 mmol), 3-chloro-2-methyl-1-propene (1.08 g, 12.0 mmol), and potassium carbonate (2.67 g, 19.38 mmol), the procedure of Reference Example 41 was followed (reaction and post-treatment) to obtain 2.43 g of a crude ether. The obtained crude (2.43 g) was allowed to react and post-treated in a manner similar to that Reference Example 47, followed by purifying by silica gel column chromatography(ether:hexane =1:1). As a result, 1.37 g of the title compound was obtained as a colorless solid (54.4%).

Workup

  1. custom(reaction and post-treatment)
  2. customThe obtained crude (2.43 g)
  3. customto react
  4. additionpost-treated in a manner similar to that Reference Example 47
  5. customby purifying by silica gel column chromatography(ether:hexane =1:1)

Sources & evidence

ORD record
ord-b3713ef1a7e44f6386b17e22253f349c
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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