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

HRID 1674631ノート

反応式

HRID 1674631 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-724e8131a59c4e38bed2cb1e209151f3
出典データセット
uspto-grants-2011_08
特許番号
US08003654B2

反応ノート

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