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Sodium Methoxide → 2-Methyl-2-(3,3,3-trifluoro-propylsulfanyl)-propionic acid ethyl ester

HRID 386920
ノート
印刷プレビュー

反応式

HRID 386920 の反応式
[CH2:1]([O:3][C:4](=[O:12])[C:5]([S:8][C:9](=O)[CH3:10])([CH3:7])[CH3:6])[CH3:2].[F:13][C:14]([F:29])([F:28])CCOS(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]([CH3:7])([S:8][CH2:9][CH2:10][C:14]([F:29])([F:28])[F:13])[CH3:6])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10942334Sodium MethoxideHCID 126353403,3,3-Trifluoroprop-1-yl toluene-4-sulphonateHCID 57937863Ethyl 2-(acetylthio)-2-methylpropanoate

生成物 1

HCID 592532102-Methyl-2-(3,3,3-trifluoro-propylsulfanyl)-propionic acid ethyl ester収率 82.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2-acetylsulfanyl-2-methyl-propionic acid ethyl ester (1.7 g, 8.72 mmol), toluene-4-sulfonic acid 3,3,3-trifluoro-propyl ester (2.3 g, 8.72 mmol) and sodium methoxide (1.9 g, 34.9 mmol) in ethanol (13 mL) are heated to 130° C. in a sealed tube for 4 h. The reaction is cooled to room temperature and concentrated under reduced pressure. The residue is diluted with DCM and washed with saturated aqueous NaHCO3 solution and brine. The organic layer is dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure to afford 1.76 g of title compound as a brown solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.28 (3H, t, J=7 Hz), 1.51 (3H, s), 2.26-2.42 (2H, m), 2.76-2.85 (2H, m), 4.18 (2H, q, J=6.96 Hz)

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue is diluted with DCM
  3. washwashed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

出典と根拠

ORDレコード
ord-8fe83ec184a2435e83ccf1961143b081
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08372874B2

反応ノート

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