4-Toluenesulfonyl chloride → [(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate

HRID 60695ノート

反応式

HRID 60695 の反応式
[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[O:7][C@H:8]([C@H:10]([OH:13])[CH2:11][OH:12])[CH2:9][C@H:4]2[O:3]1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH3:25][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:12][CH2:11][C@H:10]([C@H:8]2[O:7][C@@H:5]3[O:6][C:2]([CH3:14])([CH3:1])[O:3][C@@H:4]3[CH2:9]2)[OH:13])(=[O:23])=[O:22])=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 11084935(R)-1-((3AR,5S,6AR)-2,2-Dimethyltetrahydrofuro[2,3-D][1,3]dioxol-5-YL)ethane-1,2-diol

生成物 1

HCID 15473566[(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate収率 74%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of (1R)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol (100 g, 490 mmol) in dry pyridine (1000 mL) was added p-toluenesulfonyl chloride (139 g, 735 mmol) at 0° C. After being stirred at room temperature for 12 hours, the resulted solution was quenched by water (100 mL) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:10 to 1:3 EtOAc in petroleum ether) to afford 130 g of [(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate (compound 6a) as a slight yellow oil.

後処理

  1. customthe resulted solution was quenched by water (100 mL)
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 1:10 to 1:3 EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-6f26cc8ea12e4ece879f4c629c42d544
出典データセット
uspto-grants-2016_09
特許番号
US09441008B2

反応ノート

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