Methyl Methacrylate → HCID 86731823, compound

HRID 1846974Notes

Reaction equation

HRID 1846974 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].CC(C)([O-])C.[K+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:30])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)=[CH:17][C:16]=1[F:31]>O1CCCC1>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:30])[CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH2:3][CH:2]([CH3:4])[C:1]([O:6][CH3:7])=[O:5])=[CH:17][C:16]=1[F:31]

Participants

5

Reactant 3

HCID 6658Methyl MethacrylateHCID 23665647Potassium tert-butoxideHCID 86731822HCID 86731822, compound

Product 1

HCID 86731823HCID 86731823, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl methacrylate (125.0 g, 1097 mmol) and potassium tert-butoxide (1 M in tetrahydrofuran, 115 mL, 115 mmol) were sequentially added to a solution of 1-(4-chloro-3-fluorophenyl)-2-(3-chlorophenyl)ethanone (327.0 g, 1160 mmol, Example 4, Step B) in anhydrous tetrahydrofuran (2.61 L), at 0° C. The reaction mixture was stirred for 1 hour at 0° C. and then warmed to ambient temperature and stirred for 12 hours. On completion, the reaction was quenched with water (1.0 L) and extracted with ethyl acetate (2×2.5 L). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to get the crude material which was purified by flash column chromatography (silica gel: 60 to 120 mesh, product eluted in 4% ethyl acetate in hexane) affording the title compound (mixture of diastereomers) as light yellow liquid.

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for 12 hours
  3. customOn completion, the reaction was quenched with water (1.0 L)
  4. extractionextracted with ethyl acetate (2×2.5 L)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto get the crude material which
  9. customwas purified by flash column chromatography (silica gel: 60 to 120 mesh, product eluted in 4% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4c754db4bdc34781b8743eea508519b8
Source dataset
uspto-grants-2015_02
Patent number
US08952036B2

Reaction notes

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