Triphenylphosphine → Methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate

HRID 1251930ノート

反応式

HRID 1251930 の反応式
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:21][N:22]1[C:26]([CH2:27][CH:28]([C:30]2[S:31][CH:32]=[CH:33][N:34]=2)O)=[CH:25][N:24]=[CH:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([O:18][CH:28]([C:30]3[S:31][CH:32]=[CH:33][N:34]=3)[CH2:27][C:26]3[N:22]([CH3:21])[CH:23]=[N:24][CH:25]=3)=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 183244102-(1-Methylimidazol-5-yl)-1-(thiazol-2-yl)ethanolHCID 18324453Methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate

生成物 1

HCID 18324499Methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of methyl 2-(4-fluorophenethyl)-5-hydroxybenzoate (1.83 g, 6.7 mmol), 2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethanol (1.40 g, 6.68 mmol) and triphenylphosphine (2.10 g, 8.0 mmol) in tetrahydrofuran (25 ml) was stirred at ambient temperature under a nitrogen atmosphere. DEAD (1.39 g, 1.25 ml 8.0 mmol) was added dropwise to the solution. (The reaction was maintained at ambient temperature ±2° C.). The orange solution was then stirred at ambient temperature under a nitrogen atmosphere for 16 hours. The tetrahydrofiran solution was evaporated to dryness to give an oil. Purification by flash column chromatography eluting with ethyl acetate, ethyl acetate/methanol (9:1 and 4:1) gave methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate (2.07 g, 67%) as a clear oil.

後処理

  1. temperature(The reaction was maintained at ambient temperature ±2° C.)
  2. stirringThe orange solution was then stirred at ambient temperature under a nitrogen atmosphere for 16 hours
  3. customThe tetrahydrofiran solution was evaporated to dryness
  4. customto give an oil
  5. customPurification by flash column chromatography
  6. washeluting with ethyl acetate, ethyl acetate/methanol (9:1 and 4:1)

出典と根拠

ORDレコード
ord-cd43111c01b94a9795f823b34edf47bb
出典データセット
uspto-grants-2002_01
特許番号
US06342765B1

反応ノート

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