4-Toluenesulfonyl chloride → [(2S)-oxolan-2-yl]methyl 4-methylbenzene-1-sulfonate

HRID 717230ノート

反応式

HRID 717230 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(N(CC)CC)C>C(Cl)Cl>[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

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 637528(2S)-(+)-2-(Hydroxymethyl)tetrahydrofuran

生成物 1

HCID 7033051[(2S)-oxolan-2-yl]methyl 4-methylbenzene-1-sulfonate収率 65%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To (S)-(tetrahydrofuran-2-yl)methanol (2.0 g, 20 mmol) in CH2Cl2 (10 mL) at about 0° C. was added p-toluenesulfonyl chloride (4.2 g, 22.00 mmol), followed by drop-wise addition of triethylamine (5.6 mL, 40.0 mmol). The resulting solution was kept at 0° C. for 2 hours, and then at room temperature for another 2 hours. The reaction mixture was concentrated to dryness and diethylether (200 mL) and water (100 mL) were added. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated to yield the title compound (2.3 g, 13.00 mmol, 64%) as a colorless oil, which was used in the next step without purification.

後処理

  1. waitat room temperature for another 2 hours
  2. concentrationThe reaction mixture was concentrated to dryness and diethylether (200 mL) and water (100 mL)
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-cabacec7484a42a198bdd59132a64059
出典データセット
uspto-grants-2015_11
特許番号
US09193713B2

反応ノート

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