4-Toluenesulfonyl chloride → (Oxan-3-yl)methyl 4-methylbenzene-1-sulfonate

HRID 78487

反応式

HRID 78487 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:19][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:8][CH2:7][CH:3]2[CH2:4][CH2:5][CH2:6][O:1][CH2:2]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

参加物

5

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 85769Tetrahydro-2H-pyran-3-methanol

生成物 1

HCID 86618913(Oxan-3-yl)methyl 4-methylbenzene-1-sulfonate

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (tetrahydropyran-3-yl)-methanol (Matrix, 1.67 g, 14.4 mmol) in 15 mL of CH2Cl2 and 15 mL of pyridine was added p-toluenesulfonyl chloride (2.9 g, 15.1 mmol) in portions over 10 minutes. The mixture stirred at ambient temperature for 18 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous phase was extracted three 5 mL of portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 70% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 288 (M+NH4)+.

後処理

  1. customwas quenched with 10 mL of saturated, aqueous NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted three 5 mL of portions of CH2Cl2
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification via column chromatography (SiO2, 70% hexanes in ethyl acetate)

出典と根拠

ORDレコード
ord-25715a1446204b478a238d2771de1968
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

関連ノート

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