Dichloromethane → HCID 22994360, compound

HRID 1167818Notes

Reaction equation

HRID 1167818 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10](=[O:29])[O:11][C:12]3[C:17]([C:18]=2[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:16][CH:15]=[C:14]([O:27][CH3:28])[CH:13]=3)=[CH:5][CH:4]=1.Cl.Cl[CH2:34][CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CN(C=O)C.CO.CCOC(C)=O>[F:31][C:2]([F:30])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10](=[O:29])[O:11][C:12]3[C:17]([C:18]=2[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:34][CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:22][CH:21]=2)=[CH:16][CH:15]=[C:14]([O:27][CH3:28])[CH:13]=3)=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 22994355HCID 22994355, compound

Product 1

HCID 22994360HCID 22994360, compoundYield 64.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4-trifluoromethylphenyl)-4-(4-hydroxybenzyl)-7-methoxychromen-2-one (6.0 g, 14 mmol), 1-(2-chloroethyl)pyrrolidine hydrochloride (3.3 g, 22.5 mmol), and K2CO3 (6.6 g, 47.8 mmol) in 30 mL of DMF was warmed at 120° C. for 2 hours. Solvent was removed under reduced pressure. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried and concentrated to provide a dark brown oil. Flash chromatography (CH2Cl2:EtOAc:MeOH:TEA) provided the desired product (4.7 grams, 64%). 1H NMR (300 MHz, DMSO-d6) δ 7.79 (d, 2H, J=8.1 Hz), 7.58 (d, 2H, J=8.1 Hz), 7.51 (d, 1H, J=9.0 Hz), 7.08 (d, 2H, J=8.9 Hz), 7.06 (d, 1H, J=2.5 Hz), 6.87 (dd, 1H, J=2.5, 9.0 Hz), 6.82 (d, 2H, J=8.9 Hz), 4.08 (t, 2H J=5.0 Hz), 3.96 (s, 2H), 3.84 (s, 3H), 3.17-3.12 (m, 2H), 2.94-2.88 (m, 4H), 1.8-1.78 (m, 4H). MS (ESI) m/z 524 (M+H)+.

Workup

  1. customSolvent was removed under reduced pressure
  2. additionWater was added
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. customThe combined organic layer was dried
  5. concentrationconcentrated
  6. customto provide a dark brown oil

Sources & evidence

ORD record
ord-c68bae32a0714a818ad371f2790e6ee8
Source dataset
uspto-grants-2003_09
Patent number
US06620838B1

Reaction notes

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