Ethyl Thioglycolate → HCID 89543486、化合物

HRID 922779ノート

反応式

HRID 922779 の反応式
[N+:1](/[CH:4]=[CH:5]/[CH:6]1[CH2:8][CH2:7]1)([O-:3])=[O:2].[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:10][SH:11]>C1COCC1>[CH:6]1([CH:5]([S:11][CH2:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][N+:1]([O-:3])=[O:2])[CH2:8][CH2:7]1

参加物

4

反応物 2

HCID 12185Ethyl ThioglycolateHCID 14978083Cyclopropane, (2-nitroethenyl)-, (E)-

生成物 1

HCID 89543486HCID 89543486、化合物収率 94.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(E)-(2-Nitrovinyl)cyclopropane (4-11, 750 mg, 6.63 mmol) was taken up in THF (20 mL). To this was added ethyl thioglycolate (0.88 mL, 7.98 mmol) then TEA (1.2 mL, 8.61 mmol) at rt. After stirring overnight the mixture was concentrated. The crude product was subjected to silica gel chromatography (40 g, 0-20% EtOAc/hexanes, 10 minute gradient) to afford ethyl 2-((1-cyclopropyl-2-nitroethyl)thio)acetate (4-12, 1.46 g, 94%) as a clear oil. 1H NMR (399 MHz, CDCl3): δ 4.73-4.58 (m, 2H); 4.21 (q, J=7.1 Hz, 2H); 3.34 (d, J=6.2 Hz, 2H); 2.93 (dt, J=9.9, 7.2 Hz, 1H); 1.30 (t, J=7.1 Hz, 3H); 1.00-0.90 (m, 1H); 0.69 (dd, J=8.0, 1.6 Hz, 2H); 0.47-0.36 (m, 2H).

後処理

  1. customat rt
  2. concentrationwas concentrated
  3. customwas subjected to silica gel chromatography (40 g, 0-20% EtOAc/hexanes, 10 minute gradient)

出典と根拠

ORDレコード
ord-e7652e7abd3d4b5c8cccbcda51d4bdbf
出典データセット
uspto-grants-2016_03
特許番号
US09278960B2

反応ノート

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