Water → HCID 117701775, compound

HRID 1507442Notes

Reaction equation

HRID 1507442 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([CH3:22])=[C:8]([CH:12]3[CH2:17][CH2:16][N:15]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:14][CH2:13]3)[O:9]2)=[CH:4][CH:3]=1.[CH2:24](Br)[CH:25]=[CH2:26].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:26]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([CH3:22])=[C:8]([CH:12]3[CH2:17][CH2:16][N:15]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:14][CH2:13]3)[O:9]2)=[CH:4][CH:3]=1)[CH:25]=[CH2:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 117701717HCID 117701717, compound

Product 1

HCID 117701775HCID 117701775, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 7-hydroxy-3-methyl-2-(1-propanoylpiperidin-4-yl)-4H-chromen-4-one (1.00 g, 3.17 mmol) obtained in Example 31-2, allyl bromide (560 μL, 6.34 mmol), and potassium carbonate (613 mg, 4.44 mmol) in acetone (20 mL) was heated with stirring at a bath temperature of 55° C. for 20 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure to obtain 947 mg of the title compound (yield: 84%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c3aabce9c9c4e439887f97c9513b7c0
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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