Diethyl nitromalonate → Methyl 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylate

HRID 1804472ノート

反応式

HRID 1804472 の反応式
[F:1][C:2]([F:14])([F:13])[CH2:3][CH2:4][C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+:15]([CH:18](C(OCC)=O)[C:19]([O:21][CH2:22]C)=[O:20])([O-])=[O:16].F[P-](F)(F)(F)(F)F.C([N+]1C=CN(C)C=1)CCC>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:7]1([C:6]2[O:16][N:15]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:5]=2[CH2:4][CH2:3][C:2]([F:13])([F:14])[F:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 3

HCID 97657Diethyl nitromalonateHCID 27341741-Butyl-3-methylimidazolium hexafluorophosphateHCID 58537198Benzene, (5,5,5-trifluoro-1-pentyn-1-yl)-

生成物 1

HCID 67454167Methyl 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylate収率 22.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (5,5,5-trifluoropent-1-ynyl)benzene (215 mg, 1.09 mmol), diethyl nitromalonate (0.758 mL, 4.34 mmol), and 1-butyl-3-methylimidazolium hexafluorophosphate (0.023 mL, 0.108 mmol) in toluene (3 mL) was heated to 170° C. for 150 minutes. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (10 mL), washed with brine (10 mL), and dried over anhydrous sodium sulfate. Concentration followed by purification by silica gel chromatography with hexanes/ethyl acetate (9/1) provided methyl 5-phenyl-4-(3,3,3-trifluoropropyl)isoxazole-3-carboxylate (72 mg). The compound had an HPLC ret. time=3.61 min.−Column. YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100.

後処理

  1. washwashed with water (10 mL)
  2. washwashed with brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationConcentration
  5. customfollowed by purification by silica gel chromatography with hexanes/ethyl acetate (9/1)

出典と根拠

ORDレコード
ord-7b6e50ec88564368b7715c8330c5648f
出典データセット
uspto-grants-2013_01
特許番号
US08354398B2

反応ノート

読み込み中…