Methyl Methacrylate → HCID 58573298, compound

HRID 1846967Notes

Reaction equation

HRID 1846967 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[Cl:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[O:17])[CH:12]=[CH:13][CH:14]=1.CC(C)([O-])C.[K+]>O1CCCC1>[Cl:8][C:9]1[CH:10]=[C:11]([CH:15]([C:16]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[O:17])[CH2:3][CH:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6658Methyl MethacrylateHCID 23665647Potassium tert-butoxideHCID 58573710HCID 58573710, compound

Product 1

HCID 58573298HCID 58573298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl methacrylate (12.65 mL, 119 mmol) was added to a solution of 2-(3-chlorophenyl)-1-(4-chlorophenyl)ethanone (30 g, 113 mmol, Example 1, Step A) in tetrahydrofuran (283 mL). Potassium tert-butoxide (1.27 g, 11.3 mmol) was then added and the reaction was stirred at room temperature for 2 days. The solvent was removed under a vacuum and replaced with 300 mL of ethyl acetate. The organic phase was washed with brine (50 mL), water (3×50 mL), and brine (50 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated under a vacuum to afford methyl 4-(3-chlorophenyl)-5-(4-chlorophenyl)-2-methyl-5-oxopentanoate as an approximately 1:1 mixture of diastereomers.

Workup

  1. customThe solvent was removed under a vacuum
  2. washThe organic phase was washed with brine (50 mL), water (3×50 mL), and brine (50 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-047bef71501e41bf8e8f2a459b3650cf
Source dataset
uspto-grants-2015_02
Patent number
US08952036B2

Reaction notes

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