Dichloromethane → (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

HRID 78464

反応式

HRID 78464 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.C(Cl)Cl.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:8][CH2:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 2773573(Oxan-4-yl)methanol

生成物 1

HCID 19077576(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of tetrahydro-2H-pyran-4-ylmethanol (Combi-Blocks, 2.0 g, 17.2 mmol) in 10 mL of of CH2Cl2 and 10 mL of of pyridine was added p-toluenesulfonyl chloride (3.5 g, 18.1 mmol) in portions over 15 minutes. The mixture stirred at ambient temperature for 16 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with three 10 mL portions of CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.05-1.25 (m, 2H), 1.40-1.53 (m, 2H), 1.73-1.94 (m, 1H), 2.43 (s, 3H), 3.14-3.28 (m, 2H), 3.71-3.84 (m, 2H), 3.88 (d, J=6.4 Hz, 2H), 7.48 (d, J=8.5 Hz, 2H), 7.79 (d, J=8.5 Hz, 2H); 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 layer was extracted with three 10 mL portions of CH2Cl2
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e9e415c09f724960b9a0817091722eb7
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

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