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4-Toluenesulfonyl chloride → HCID 20148930, 화합물

HRID 569303
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HRID 569303 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 73974-Toluenesulfonyl chlorideHCID 10614TriphenylmethaneHCID 433294Lithium ChlorideHCID 14098158HCID 14098158, 화합물HCID 178418348HCID 178418348, 화합물

생성물 1

HCID 20148930HCID 20148930, 화합물

시약·촉매·용매 3

HCID 962
Water
용매
HCID 3283Diethyl Ether용매4회
HCID 12679Hexamethylphosphoramide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-82aa5d3cc6ce4b54b0bf59d26e19d50c
출처 데이터셋
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04731471

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