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

HRID 1674629ノート

反応式

HRID 1674629 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=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].C[Li].[CH3:26]COCC>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:9])[CH3:26])=[CH:4][C:3]=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 57511304N-(2-chloro-5-formyl-phenyl)-3,4-dimethoxy-benzenesulfonamideHCID 178418348HCID 178418348、化合物

生成物 1

HCID 57511305N-[2-chloro-5-(1-hydroxy-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide収率 100%

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-(2-chloro-5-formyl-phenyl)-3,4-dimethoxy-benzenesulfonamide (1.77 g, 5 mmol) in THF (20 mL) at −78° C. was added dropwise a solution of methyl lithium in ether (1.6 M, 8.6 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 dried under hv to give the desired product (1.8 g, 100%) as a yellowish oil.

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 dried under hv

出典と根拠

ORDレコード
ord-e0194d3c5ab441e29dd0851840870840
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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