N,N-Diethylaniline → 8-allyl-7-hydroxy-4-methyl-chromen-2-one

HRID 490038Notes

Reaction equation

HRID 490038 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([CH3:16])=[CH:10][C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)C=C.C(N(CC)[C:20]1[CH:25]=CC=C[CH:21]=1)C>>[CH2:25]([C:14]1[C:5]([OH:4])=[CH:6][CH:7]=[C:8]2[C:13]=1[O:12][C:11](=[O:15])[CH:10]=[C:9]2[CH3:16])[CH:20]=[CH2:21]

Participants

3

Reactant 2

HCID 7061N,N-DiethylanilineHCID 2389527-(Allyloxy)-4-methyl-2H-chromen-2-one

Product 1

HCID 57131038-allyl-7-hydroxy-4-methyl-chromen-2-oneYield 88%

Conditions

Temperature
250 °C

Procedure

7-Allyloxy-4-methylcoumarin 2 (1.0 g, 4.62 mmol) was dissolved in N,N-diethylaniline (8 mL) in a sealed vial and heated to 250° C. for 25 min under microwave. The reaction mixture was then cooled, during which some of the product precipitated. Hexane (10 mL) was added in order to precipitate out the remaining product. The precipitate was filtered, washed with hexane, and dried under vacuum to yield 3 as a pale-yellow solid (0.88 g, 88%). TLC (hexane/ethyl acetate, 1:3): Rf=0.5. mp 204° C. 1H NMR (CDCl3/CD3OD, 500 MHz) δ 2.43 (s, 3H, CH3), 3.57 (d, J=6.0 Hz, 2H, CH2), 4.95 (d, J=10.0 Hz, 1H), 5.04 (d, J=17.0 Hz, 1H), 5.97 (m, 1H), 6.10 (s, 1H), 6.86 (d, J=9.0 Hz, 1H), 7.46 (d, J=9.0 Hz, 1H). 13C NMR (CDCl3/CD3OD, 125 MHz) δ 18.85, 27.66, 110.78, 113.20, 113.73, 114.93, 115.41, 124.38, 136.16, 153.89, 155.88, 160.18, 163.92. ESIMS calcd for C13H13O3 [M+H]+ 217.1. Found 217.2.

Workup

  1. temperatureThe reaction mixture was then cooled, during which some of the product
  2. customprecipitated
  3. additionHexane (10 mL) was added in order
  4. customto precipitate out the remaining product
  5. filtrationThe precipitate was filtered
  6. washwashed with hexane
  7. customdried under vacuum

Sources & evidence

ORD record
ord-77793a89bff742dd94d4837e00b3c8fe
Source dataset
uspto-grants-2009_05
Patent number
US07527934B2

Reaction notes

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