Oxiranemethanol, 4-methylbenzenesulfonate, (S)- → Toluene-4-sulfonic acid 2-(S)-hydroxy-5-methylhexyl ester

HRID 20354

反応式

HRID 20354 の反応式
[CH2:1]([Mg]Br)[CH:2]([CH3:4])[CH3:3].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:17][CH2:18][C@H:19]2[O:21][CH2:20]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1>O1CCCC1>[OH:21][C@@H:19]([CH2:20][CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:18][O:17][S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

参加物

4

反応物 2

HCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-HCID 178418816HCID 178418816、化合物

生成物 1

HCID 87498269Toluene-4-sulfonic acid 2-(S)-hydroxy-5-methylhexyl ester収率 75.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
2.5 °C

実験手順

Add dropwise over 5 minutes isobutylmagnesium bromide (4.4 mL, 8.8 mmol, 2 M in diethyl ether) to a solution of lithium tetrachlorocuprate (4.4 mL, 0.44 mmol, 0.1 M in tetrahydrofuran) cooled to −35-40° C. Dissolve (2S)-(+)-glycidyl tosylate (1.674 g, 7.73 mmol) in tetrahydrofuran (8 mL), cool to −40° C. and cannulate into the stirring Grignard reaction flask. Quench with saturated aqueous ammonium chloride (25 mL), pour supernate into saturated aqueous ammonium chloride (25 mL) and water and shake well. Wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 10:90 to 25:75 ethyl acetate:hexanes) to give the desired compound (1.6711 g, 75%).

後処理

  1. customcannulate into the stirring Grignard reaction flask
  2. customQuench with saturated aqueous ammonium chloride (25 mL)
  3. additionpour supernate into saturated aqueous ammonium chloride (25 mL) and water
  4. washWash with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 10:90 to 25:75 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-3e73c66220eb47a0913b0234fe1c8597
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

関連ノート

読み込み中…