Methyl Acrylate → HCID 86706689, compound

HRID 1468077Notes

Reaction equation

HRID 1468077 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][C:3]=1[CH3:12].[C:13]([O:17]C)(=O)[CH:14]=[CH2:15].[CH3:19][C:20](C)([O-])C.[K+].[OH-].[K+]>[Cl-].[Na+].O.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:15][CH2:14][C:13](=[O:17])[CH2:20][CH2:19]3)[C:8]2=[O:11])=[CH:4][C:3]=1[CH3:12]

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 14797Potassium HydroxideHCID 23665647Potassium tert-butoxideHCID 69203162HCID 69203162, compound

Product 1

HCID 86706689HCID 86706689, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 6-bromo-5-methyl-2,3-dihydro-1H-inden-1-one (commercially available), 1.45 g, 6.42 mmol) and methyl acrylate (1.28 mL, 14.1 mmol) in 2-Me THF (6 mL) cooled to 0° C. was added potassium tert-butoxide (0.864 g, 7.70 mmol) in portions. After stirring for 2 h at r.t., water (9.0 mL) and potassium hydroxide (0.36 g, 6.42 mmol) were added and the mixture was heated at reflux overnight. The mixture was allowed to cool to r.t. and brine was added. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to yield 1.38 g (70% yield) of the title compound: 1H NMR (500 MHz, CDCl3) δ ppm 1.86 (m, 2 H) 2.20 (m, 2 H) 2.45 (m, 2 H) 2.51 (s, 3 H) 2.71 (dt, 2 H) 3.13 (s, 2 H) 7.38 (s, 1 H) 7.95 (m, 1 H): MS (ES+) m/z 307, 309 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureto cool to r.t.
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with DCM
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e213320cc121493f8b1099b336fbed7d
Source dataset
uspto-grants-2015_04
Patent number
US09000183B2

Reaction notes

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