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Iodoethane → 4-(2-Ethoxy-naphthalen-1-ylmethyl)-1-[4(1-ethoxy-propyl)-2,6-dimethylphenyl]-3,5-diethyl-1H-pyrazole

HRID 1740114
ノート
印刷プレビュー

反応式

HRID 1740114 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:16][C:17]1[C:18]([CH2:36][CH3:37])=[N:19][N:20]([C:24]2[C:29]([CH3:30])=[CH:28][C:27]([CH:31]([OH:34])[CH2:32][CH3:33])=[CH:26][C:25]=2[CH3:35])[C:21]=1[CH2:22][CH3:23])[CH3:4].I[CH2:39][CH3:40].C(Cl)Cl>O1CCCC1>[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[CH2:16][C:17]1[C:18]([CH2:36][CH3:37])=[N:19][N:20]([C:24]2[C:25]([CH3:35])=[CH:26][C:27]([CH:31]([O:34][CH2:39][CH3:40])[CH2:32][CH3:33])=[CH:28][C:29]=2[CH3:30])[C:21]=1[CH2:22][CH3:23])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6340Iodoethane2 回HCID 6344DichloromethaneHCID 24758Sodium hydride3 回HCID 218373291-{4-[4-(2-Ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-propan-1-ol

生成物 1

HCID 218373424-(2-Ethoxy-naphthalen-1-ylmethyl)-1-[4(1-ethoxy-propyl)-2,6-dimethylphenyl]-3,5-diethyl-1H-pyrazole収率 146.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (60% mineral oil dispersion, 0.031 g, 0.78 mmol) was added portionwise to a solution of 1-{4-[4-(2-ethoxy-naphthalen-1-ylmethyl)-3,5-diethyl-pyrazol-1-yl]-3,5-dimethylphenyl}-propan-1-ol (0.123 g, 0.26 mmol) in 0.5 ml anhydrous tetrahydrofuran. After stirring 5 minutes, iodoethane (0.104 ml, 1.3 mmol) was added and the resulting mixture was stirred for 16 hours at ambient temperature. A second portion of sodium hydride (0.031 g of a 60% sodium hydride mineral oil dispersion; 0.78 mmol) was added, followed by a second portion of iodoethane (0.104 ml, 1.3 mmol). After stirring at ambient temperature for 4 hours, the reaction mixture was well-mixed with methylene chloride/aqueous sodium bicarbonate (10 ml of each). The aqueous phase was then twice extracted with 10 ml portions of fresh methylene chloride. The combined organic extracts were then dried over anhydrous sodium sulfate and concentrated in vacuo to afford a 190 mg residue. Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexanes=1:4 in volume) afforded the title compound (45 mg) as an oil.

後処理

  1. stirringthe resulting mixture was stirred for 16 hours at ambient temperature
  2. addition0.78 mmol) was added
  3. stirringAfter stirring at ambient temperature for 4 hours
  4. extractionThe aqueous phase was then twice extracted with 10 ml portions of fresh methylene chloride
  5. dry with materialThe combined organic extracts were then dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-dd4bc209f2424709a4f985b907ea62f1
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05968944

反応ノート

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