Triethylamine → HCID 23614673, compound

HRID 731759Notes

Reaction equation

HRID 731759 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:14][NH:13][C:12](=[O:15])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Cl:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([O:1][C:2]2[CH:3]=[C:4]([CH:10]3[CH2:14][NH:13][C:12](=[O:15])[CH2:11]3)[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 742994-Chlorophenylboronic acidHCID 10130484HCID 10130484, compound

Product 1

HCID 23614673HCID 23614673, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(3-hydroxy-4-methoxyphenyl)-2-pyrrolidone (63 mg, 0.3 mmol), 4-chlorophenylboronic acid (61 mg, 0.45 mmol), copper (II) acetate (54 mg, 0.3 mmol), triethylamine (152 mg, 1.5 mmol), dichloromethane (3 mL) and small amount of molecular sieves was allowed to stir at ambient temperature. After 18 hours, the mixture was filtered over celite and the filtrate was concentrated in vacuo. The resulting residue was dissolved in 30 mL of ethyl acetate and washed successively with saturated aqueous sodium bicarbonate solution and brine. Purification by flash column chromatography (ethyl acetate/hexane 1:1 to methanol/dichloromethane 3:97) gave 26 mg (27%) of 4-(3-(4-chlorophenyloxy)-4-methoxyphenyl)-2-pyrrolidone: 1H NMR (300 MHz, CDCl3) δ 7.24 (d, J=9.2 Hz, 2H), 7.03 (d, J=8.4 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 6.87 (s, 1H), 6.83 (d, J=9.2 Hz, 2H), 5.83 (b, 1H), 3.80 (s, 3H), 3.72 (t, J=8.4 Hz, 1H), 3.65-3.62 (m, 1H), 3.34 (t, J=8.4 Hz, 1H), 2.68 (dd, J=16.8, 8.8 Hz, 1H), 2.41 (dd, J=16.8, 9.2 Hz, 1H).

Workup

  1. filtrationthe mixture was filtered over celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in 30 mL of ethyl acetate
  4. washwashed successively with saturated aqueous sodium bicarbonate solution and brine
  5. customPurification by flash column chromatography (ethyl acetate/hexane 1:1 to methanol/dichloromethane 3:97)

Sources & evidence

ORD record
ord-137dfb8ce73546b9a096e967e99a3f81
Source dataset
uspto-grants-2009_09
Patent number
US07585882B2

Reaction notes

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