Methanesulfonyl chloride → Propanoic acid, 2-[(methylsulfonyl)oxy]-, ethyl ester, (R)-

HRID 1487179ノート

反応式

HRID 1487179 の反応式
[OH:1][C@H:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:9][S:10](Cl)(=[O:12])=[O:11]>C1COCC1>[CH3:9][S:10]([O:1][C@H:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:12])=[O:11]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 637513ethyl (2R)-2-hydroxypropanoate

生成物 1

HCID 2723759Propanoic acid, 2-[(methylsulfonyl)oxy]-, ethyl ester, (R)-収率 60.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
12.5 °C

実験手順

(R)-ethyl 2-hydroxypropanoate (15 g, 0.127 mol) and TEA (15.4 g, 0.15 mol) were added to THF and then cooled to 10-15° C. Then MsCl (15 g, 0.13 mol) was added to the solution dropwise with cooling while maintaining the temperature in the range of 10-15° C. at about 2 hours. The mixture was allowed to warm to about 20° C. and the solid was filtered off. The solution was washed with water and dried, concentrated to afford (R)-ethyl 2-(methylsulfonyloxy)propanoate (15 g, 60%). 1H NMR (400 MHz, CDCl3) δ ppm, 5.11-5.14 (q, 1H), 4.24-4.29 (m, 2H), 2.81-3.17 (q, 3H, J=7.2 Hz), 1.61-1.43 (d, 3H, J=7.6 Hz), 1.30-1.32 (m, 3H).

後処理

  1. temperaturewith cooling
  2. temperaturewhile maintaining the temperature in the range of 10-15° C. at about 2 hours
  3. temperatureto warm to about 20° C.
  4. filtrationthe solid was filtered off
  5. washThe solution was washed with water
  6. customdried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-05e472a86a05404490d5951d59894000
出典データセット
uspto-grants-2016_08
特許番号
US09428508B2

反応ノート

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