Triphenylphosphine → ethyl 1-({5-methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257439ノート

反応式

HRID 1257439 の反応式
[CH3:1][C:2]1[O:6][C:5]([CH2:7]O)=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.[NH:19]1[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[N:20]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([CH2:7][N:19]2[CH:23]=[C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:21]=[N:20]2)=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1

参加物

7

反応物 5

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 66939730{5-Methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methanol

生成物 1

HCID 66939161ethyl 1-({5-methyl-4-[3-(trifluoromethyl)phenyl]furan-2-yl}methyl)-1H-pyrazole-4-carboxylate収率 33.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of the compound (0.40 g) obtained in Example 128d, ethyl 1H-pyrazole-4-carboxylate (0.26 g) and triphenylphosphine (0.49 g) in tetrahydrofuran (5 mL) was cooled in an ice bath, diisopropyl azodicarboxylate (0.36 mL) was added, and the mixture was stirred at the same temperature for 1 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane/ethyl acetate) to give the title compound (0.20 g) as a yellow oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-5d7162b648d94ffdbf2c2139c9857ea8
出典データセット
uspto-grants-2013_06
特許番号
US08461348B2

反応ノート

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