HCID 16098369, compound → 4-(4-chlorophenyl)-3-phenyl-2-Butanone

HRID 1446378Notes

Reaction equation

HRID 1446378 reaction equation
CON(C)[C:4](=[O:20])[CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[CH3:22][Mg]Br>O1CCCC1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4](=[O:20])[CH3:22])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 16098369HCID 16098369, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 2293694-(4-chlorophenyl)-3-phenyl-2-Butanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide (Step C, 16 g, 53 mmol, dried by azeotroping with toluene) in anhydrous tetrahydrofuran (200 mL) at 0° C. was added methylmagnesium bromide (3 M in ether, 35 mL, 0.11 mol). After stirring at 0° C. for 2 h, the reaction was quenched with methanol (5 mL) and 2 M hydrochloric acid (50 mL). The volatile materials were removed by concentrating on a rotary evaporator and the residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL). The organic layer was separated, and the aqueous layer was extracted with ether (2×200 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to dryness to give the title compound, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.45-7.02 (m, 9H), 4.08 (dd, 1H), 3.34 (dd, 1H), 2.90 (dd, 1H), 2.03 (s, 3H).

Workup

  1. customthe reaction was quenched with methanol (5 mL) and 2 M hydrochloric acid (50 mL)
  2. customThe volatile materials were removed
  3. concentrationby concentrating on a rotary evaporator
  4. customthe residue partitioned between saturated ammonium chloride (200 mL) and ether (200 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ether (2×200 mL)
  7. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2323ff3fb36a4e1498a97ee4cab477b2
Source dataset
uspto-grants-2010_02
Patent number
US07667053B2

Reaction notes

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