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

HRID 20354

반응식

HRID 20354 반응식
[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]

참가 물질

4

반응물 2

HCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-HCID 178418816HCID 178418816, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
2.5 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3e73c66220eb47a0913b0234fe1c8597
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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