Ethanol → [2'-(N-t-Butylsulfamoyl)-5'n-propylbiphenyl-4-yl]methanol

HRID 1198675

反応式

HRID 1198675 の反応式
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=1B(O)O)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=1.[OH-].[Na+].CCO>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=1[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 701194-Bromobenzyl alcoholHCID 19939476(2-(N-(tert-Butyl)sulfamoyl)-5-propylphenyl)boronic acid

生成物 1

HCID 19939403[2'-(N-t-Butylsulfamoyl)-5'n-propylbiphenyl-4-yl]methanol

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2.80 g (9.36 mmol ) of 2-(N-t-butylsulfamoyl)-5-n-propylphenylboronic acid (from Step B) and 4-bromobenzyl alcohol (5.25 g, 3 equiv) in toluene (125 mL) was added 1.25N NaOH (32 mL), EtOH (86 mL) and tetrakis(triphenylphosphine)palladium(0) (325 mg, 3 mol %). The mixture was stirred at 100° C. under N2 for 3 hours. The reaction was concentrated and the residue was extracted with ethyl acetate. The organic solution was washed with 1N NaOH, H2O and brine. Next, the organic phase was dried over anhydrous MgSO4 and concentrated in vacuo. The product was purified by flash chromatography, eluting with 2:1 hexane-EtOAc, to provide the titled compound; Rf =0.42 (1:1 EtOAc-hexane).

後処理

  1. concentrationThe reaction was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic solution was washed with 1N NaOH, H2O and brine
  4. dry with materialNext, the organic phase was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography
  7. washeluting with 2:1 hexane-EtOAc

出典と根拠

ORDレコード
ord-9d06ee2337644cecb891377474571fe1
出典データセット
uspto-grants-1994_01
特許番号
US05281614

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