Methanesulfonyl chloride → Methyl 3-[2-[(methylsulfonyl)oxy]ethyl]-1-naphthalenecarboxylate

HRID 337603ノート

反応式

HRID 337603 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.CCN(C(C)C)C(C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:27][S:28]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:30])=[O:29]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66896170Methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate

生成物 1

HCID 86651673Methyl 3-[2-[(methylsulfonyl)oxy]ethyl]-1-naphthalenecarboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a dichloromethane (0.03 M) solution of methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate (1 eq.) from Step 2, Amine 31 and Hunig's base (1.5 eq.) was added at 0 methanesulfonyl chloride (1.3 eq.). The resulting solution was stirred at 0° C. for 30 min and then at RT for 15 min. The reaction mixture was subsequently quenched with 10% aq. HCl. The aqueous wash was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, and filtered. Concentration of the filtrate in vacuo afforded the crude title compound as a colorless oil.

後処理

  1. waitat RT for 15 min
  2. customThe reaction mixture was subsequently quenched with 10% aq. HCl
  3. washThe aqueous wash
  4. customwas separated
  5. extractionback-extracted with ether
  6. washThe combined organic extracts were washed further with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-000c422fc2324db0bf00c579bcb36652
出典データセット
uspto-grants-2014_11
特許番号
US08889714B2

反応ノート

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