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4-Toluenesulfonyl chloride → HCID 20148930、化合物

HRID 569303
ノート
印刷プレビュー

反応式

HRID 569303 の反応式
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:21][CH2:22]O)([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:24])[CH:5]=1.C1(C(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Li].C1(C)C=CC(S([Cl:55])(=O)=O)=CC=1.[Cl-].[Li+]>CN(C)P(N(C)C)(N(C)C)=O.CCOCC.O>[Cl:55][CH2:22][CH2:21][C:9]12[CH2:8][CH2:7][C:6](=[O:24])[CH:5]=[C:4]1[C:3]1[C:11](=[CH:12][C:13]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([Cl:15])[C:2]=1[Cl:1])[CH2:10]2
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 73974-Toluenesulfonyl chlorideHCID 10614TriphenylmethaneHCID 433294Lithium ChlorideHCID 14098158HCID 14098158、化合物HCID 178418348HCID 178418348、化合物

生成物 1

HCID 20148930HCID 20148930、化合物

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 3283Diethyl Ether溶媒4 回
HCID 12679Hexamethylphosphoramide溶媒

実験手順

In an atmosphere of dry nitrogen a solution of {[5,6-dichloro-9a-(2-hydroxyethyl)-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-7-yl]oxy}acetic acid (3.71 g, 10 mMole) in hexamethylphosphoramide (25 ml), anhydrous ether (50 ml) and triphenylmethane (10 mg) is stirred at 0° C. Methyllithium (12.6 ml of 1.6M) solution in ether=20 mMole) is added, dropwise with stirring, over a period of 30 minutes. A solution of p-toluenesulfonyl chloride (2 g, 10.5 mMole) in ether (15 ml) is added over a period of 30 minutes. Finally, dry lithium chloride (420 mg; 10 mMole) is added. The mixture is stirred and allowed to warm to room temperature over 20 hours. Ether (25 ml) and water (50 ml) is added and the layers separated. The organic layer is acidified with hydrochloric acid, washed four times with water (50 ml portions) and finally with a brine solution. After drying the organic phase with magnesium sulfate, the solvent is removed by evaporation at reduced pressure and the residue recrystallized from acetonitrile to give the desired product.

後処理

  1. stirringThe mixture is stirred
  2. customthe layers separated
  3. washwashed four times with water (50 ml portions)
  4. dry with materialAfter drying the organic phase with magnesium sulfate
  5. customthe solvent is removed by evaporation at reduced pressure
  6. customthe residue recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-82aa5d3cc6ce4b54b0bf59d26e19d50c
出典データセット
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04731471

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート