Methyl Acrylate → HCID 58197188, compound

HRID 1503453Notes

Reaction equation

HRID 1503453 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][CH:3]=1.[CH3:12][O:13][C:14](=[O:17])[CH:15]=[CH2:16]>O1CCOCC1.C1(C=CC(O)=CC=1)O>[CH3:12][O:13][C:14](=[O:17])[CH2:15][CH2:16][C:7]1([CH2:16][CH2:15][C:14]([O:13][CH3:12])=[O:17])[CH2:6][C:5]2[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)[C:8]1=[O:11]

Participants

5

Reactant 2

HCID 7294Methyl Acrylate2×HCID 1397781-Indanone, 6-bromo-

Product 1

HCID 58197188HCID 58197188, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 785HydroquinoneCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To 6-bromo-1-indanone (25 g, 0.12 mol) in dioxane (150 mL) was added Triton B (2.48 mL, 6.3 mmol) and hydroquinone (5 mg, 0.05 mmol). After stirring the mixture for 10 min at 50° C. methylacrylate (21.5 mL, 0.24 mol) in 50 mL dioxane was added. The mixture was stirred for 4 h at 50° C. and 14 h at RT. Then 2 mL methylacrylate was added and the reaction was stirred for 1 h at 50° C. The reaction mixture was poured onto water, extracted with EA and the solvents were evaporated. The residue was purified by MPLC (340 g silicagel, gradient:CH/EA 100:0 to 50:50) to give 3-[6-Bromo-2-(2-methoxycarbonyl-ethyl)-1-oxo-indan-2-yl]-propionic acid methyl ester (38 g, 84%).

Workup

  1. additionwas added
  2. stirringthe reaction was stirred for 1 h at 50° C
  3. additionThe reaction mixture was poured onto water
  4. extractionextracted with EA
  5. customthe solvents were evaporated
  6. customThe residue was purified by MPLC (340 g silicagel, gradient:CH/EA 100:0 to 50:50)

Sources & evidence

ORD record
ord-9854f33e94634e0ca9eef5b88e885789
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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