Diethyl Ether → N-[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide

HRID 1674631노트

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HRID 1674631 반응식
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:24])=[C:8]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].C[Li].[CH3:27]COCC>C1COCC1>[Cl:24][C:7]1[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:27])[CH3:2])=[CH:9][C:8]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 57511306N-(5-acetyl-2-chloro-phenyl)-3,4-dimethoxy-benzenesulfonamideHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 57511302N-[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of N-(5-acetyl-2-chloro-phenyl)-3,4-dimethoxy-benzenesulfonamide (1.4 g, 3.8 mmol) in THF (16 mL) at −78° C. was added dropwise a solution of methyl lithium in ether (1.6 M, 6.5 mL, 2.75 eq). The mixture was stirred at −78° C. for 30 min and then allowed to warm to RT. The mixture was partitioned between EA and NH4Cl solution, the aqueous phase was once more extracted with EA and the combined organic layers were dried over MgSO4 and concentrated. The residue was purified by chromatography on SiO2 (hex/EA 2:1, 1:1) to give the desired product (0.97 g, 67%) as a yellowish foam.

후처리

  1. temperatureto warm to RT
  2. customThe mixture was partitioned between EA and NH4Cl solution
  3. extractionthe aqueous phase was once more extracted with EA
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on SiO2 (hex/EA 2:1, 1:1)

출처 및 근거

ORD 기록
ord-724e8131a59c4e38bed2cb1e209151f3
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003654B2

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