Potassium Carbonate → HCID 9972651, compound

HRID 272800Notes

Reaction equation

HRID 272800 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:16])[O:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([OH:15])[CH:9]=2)=[O:4].C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:16])[O:7][C:8]2[CH:9]=[C:10]([O:15][CH2:14][C:13]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:11]=[CH:12][C:13]=2[CH:14]=1)=[O:4]

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 5416969Methyl 7-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate

Product 1

HCID 9972651HCID 9972651, compoundYield 135.4%

Conditions

Temperature
70 °C

Procedure

7-hydroxyl-3-coumarin carboxylic acid methyl ester (0.2g, 1 mmol) is dissolved in N,N′-dimethyl formamide (2 mL), and bromobenzyl (0.36 ml, 3 mmol) and levigated potassium carbonate (0.5 g) are added into. The resulting mixture is stirred for 12 hours at 70° C. After adding 10 mL of water, extraction is conducted with ethyl acetate, and all of ethyl acetate are combined, followed by washing with water, drying on anhydrous sodium sulfate. Then the solution is concentrated under reduced pressure to approximately 5 mL and is placed to separate out a solid, followed by filtering under reduced pressure to obtain 0.21 g of the captioned compound, yield: 67.7%. m.p.129-130° C. 1H NMR(CDCl3): δ=3.92(s, 3H), 5.19(s, 2H), 6.85(d, J=2.4 Hz, 1H), 6.95(dd, J=8.8 Hz, 2.4 Hz, 1H), 7.40(m, 5H), 7.52(d, J=8.8 Hz, 1H), 8.55(s, 1H); Elements Analysis, C18H14O5 (310): Calculated C, 69.68; H, 4.52. Found C, 69.63; H, 4.51; IR(KBr) : 3054.7, 2948.7, 1749.1, 1697.1, 1610.3, 1558.2, 1500.4, 1438.7, 1378.9, 1226.5, 1116.6, 1026, 794.5, 725.1, 692.3, 636.4 cm−1; EI-MS(m/z): 310(12, M+), 91(100).

Workup

  1. additionAfter adding
  2. extraction10 mL of water, extraction
  3. washby washing with water
  4. dry with materialdrying on anhydrous sodium sulfate
  5. concentrationThen the solution is concentrated under reduced pressure to approximately 5 mL
  6. customto separate out a solid
  7. filtrationby filtering under reduced pressure

Sources & evidence

ORD record
ord-b5868d1c83b64a8491d1c9c3acfaf368
Source dataset
uspto-grants-2008_11
Patent number
US07456205B2

Reaction notes

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