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Triphenylphosphine → 1-(4-tert-butoxyethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1748560
ノート
印刷プレビュー

反応式

HRID 1748560 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].[C:19]([O:23][CH2:24][CH2:25]O)([CH3:22])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)C)=O)=O)(C)C>O1CCCC1.C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:25][CH2:24][O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:16][CH:17]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11776TriphenylphosphineHCID 242322-(Tert-butoxy)ethan-1-olHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 866924241-(4-hydroxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

生成物 1

HCID 897349361-(4-tert-butoxyethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester収率 123.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(4-Hydroxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (500 mg) in Reference Example 39 (2), 2-tert-butoxyethanol (480 mg) and triphenylphosphine (1.06 g) in tetrahydrofuran (20 ml) was added dropwise a solution of 40% azodicarboxylic acid diisopropylester in toluene (2.14 ml) under ice-cooling, and then stirred at room temperature overnight. After completion of the reaction, water was added thereto, extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give 1-(4-tert-butoxyethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (870 mg) as a pale yellow oil.

後処理

  1. temperaturecooling
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-013471679a6f441082657b4f815af7a3
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150555B2

反応ノート

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