4-Toluenesulfonyl chloride → (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 254621

反応式

HRID 254621 の反応式
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][OH:7].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C(Cl)Cl.N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:7][CH2:6][C@H:2]2[CH2:3][CH2:4][CH2:5][O:1]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

参加物

6

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 6931745(2R)-oxolan-2-ylmethanol

生成物 1

HCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of the (R)-(tetrahydrofuran-2-yl)methanol (Aldrich, 12 g, 0.12 mol) in 40 mL CH2Cl2 and 40 mL pyridine was added 4-dimethylaminopyridine (DMAP, 0.72 g, 5.9 mmol). This mixture was cooled to 0° C. and p-toluenesulfonyl chloride (23.5 g, 0.123 mol) was added portionwise over 20 minutes. The mixture stirred at ambient temperature for 16 hours, then quenched with excess 5% aqueous HCl. The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 65% hexanes in EtOAc) provided the title compound. MS (DCI/NH3) m/z 257 (M+H)+; m/z 274 (M+NH4)+.

後処理

  1. customquenched with excess 5% aqueous HCl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (SiO2, 65% hexanes in EtOAc)

出典と根拠

ORDレコード
ord-8331b5fd8ac94518858fb1403a8e1bfb
出典データセット
uspto-grants-2011_01
特許番号
US07875640B2

関連ノート

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