Methyl Acrylate → HCID 86706703, compound

HRID 1468226Notes

Reaction equation

HRID 1468226 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[C:13]([O:17]C)(=O)[CH:14]=[CH2:15].[CH3:19][C:20](C)([O-])C.[K+].[OH-].[K+]>C1COCC1.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([CH2:15][CH2:14][C:13](=[O:17])[CH2:20][CH2:19]3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 14797Potassium HydroxideHCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86706703HCID 86706703, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-Bromo-3,4-dihydronaphthalen-1-(2H)-one (10.3 g, 45.8 mmol) and methyl acrylate (9.08 mL, 101 mmol) was dissolved in THF (55 mL) and cooled in an ice bath. Potassium tert-butoxide (6.16 g, 54.9 mmol) was added in portions. The mixture was stirred for 1.5 h at r.t. Water (80 mL) and potassium hydroxide (2.57 g, 45.8 mmol) were added and the mixture was heated to 75° C. overnight in an open system. The mixture was cooled to r.t. and filtered. The obtained solid was dried in vacuo yielding the title compound (11.5 g, 82% yield): 1H NMR (CDCl3) δ ppm 1.74-1.87 (m, 2 H), 2.15 (t, 2 H), 2.24-2.43 (m, 4 H), 2.62-2.72 (m, 2 H), 3.00 (t, 2 H), 7.16 (d, 1 H), 7.61 (dd, 1 H), 8.16 (d, 1 H); MS (ES+) m/z 307, 309 [M+H]+.

Workup

  1. temperaturecooled in an ice bath
  2. temperaturethe mixture was heated to 75° C. overnight in an open system
  3. temperatureThe mixture was cooled to r.t.
  4. filtrationfiltered
  5. customThe obtained solid was dried in vacuo

Sources & evidence

ORD record
ord-43b53562d67b472e92e79de6ccd5a91f
Source dataset
uspto-grants-2015_04
Patent number
US09000184B2

Reaction notes

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