Tetrahydrofuran → HCID 136414663, compound

HRID 645304Notes

Reaction equation

HRID 645304 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:23]([F:26])([F:25])[F:24])=[CH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[C:15]([CH3:22])[CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.CO[CH:29](OC)[N:30](C)C.[O:35]1[CH2:39]CCC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:23]([F:26])([F:24])[F:25])=[CH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:19][CH:29]=[N:30][O:35][CH3:39])=[O:18])=[C:15]([CH3:22])[CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 78373Dimethylformamide dimethyl acetalHCID 66738433HCID 66738433, compound

Product 1

HCID 136414663HCID 136414663, compound

Procedure

To a solution of 0.18 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoic acid amide representing mixed geometrical isomers (isomeric ratio of 10:1) that was synthesized according to Synthetic Example 9 in 3 mL of tetrahydrofuran, 0.11 g of N,N-dimethylformamide dimethyl acetal was added and the mixture was stirred for 2 hours at room temperature. After that, the solvent was distilled off under reduced pressure, the resulting residue was dissolved in 3 mL of tetrahydrofuran, and a solution of 45 mg of methoxyamine hydrochloride in 1 mL of water was dripped in at room temperature. After the mixture was stirred for 1.5 hours, whereinto ethyl acetate was added, an organic layer was washed twice with water and then dehydrated and dried with saturated saline followed by anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. By washing the resulting solid with a mixed solvent of diisopropylether and acetonitrile, 60 mg of aimed product was obtained as pale yellow solid.

Workup

  1. customwas synthesized
  2. distillationAfter that, the solvent was distilled off under reduced pressure
  3. dissolutionthe resulting residue was dissolved in 3 mL of tetrahydrofuran
  4. customwas dripped in at room temperature
  5. stirringAfter the mixture was stirred for 1.5 hours, whereinto ethyl acetate
  6. additionwas added
  7. washan organic layer was washed twice with water
  8. customdried with saturated saline
  9. distillationthe solvent was distilled off under reduced pressure
  10. washBy washing the resulting solid with a mixed solvent of diisopropylether and acetonitrile

Sources & evidence

ORD record
ord-96dd84b3b3fb4db0aab851af7f3a47e3
Source dataset
uspto-grants-2010_04
Patent number
US07700808B2

Reaction notes

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