Diethyl Oxalate → HCID 69968494、化合物

HRID 1166211

反応式

HRID 1166211 の反応式
[Br:1][C:2]1[S:6][C:5](Br)=[C:4]([Br:8])[C:3]=1[Br:9].C([Li])CCC.[C:15](OCC)(=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>>[CH2:19]([O:18][C:16](=[O:17])[C:15]([C:5]1[S:6][C:2]([Br:1])=[C:3]([Br:9])[C:4]=1[Br:8])=[O:21])[CH3:20]

参加物

4

反応物 3

HCID 7268Diethyl OxalateHCID 77565TetrabromothiopheneHCID 178418339Butyllithium

生成物 1

HCID 69968494HCID 69968494、化合物収率 71.3%

反応条件

温度
-18 °C

実験手順

To tetrabromothiophene (2.0 g, 5.0 mmol) in an oven dried 50 mL flask, evacuated and flushed with nitrogen, was added anhydrous diethyl ether (12 ml). The resulting solution was cooled to −18° C., then n-butyllithium (1.6 M in hexane) (3.1 ml, 5.0 mmol ) was added dropwise via a syringe. After stirring for 10 min at −18° C., diethyl oxalate (0.75 ml, 5.5 mmol) was added dropwise. Stirring was continued for 30 min, then the reaction mixture was quenched with 1N HCl. The organic layer was separated, dried over Na2SO4 and concentrated under vacuum. Purification was performed by column chromatography using hexane/ethyl acetate (20:1) to yield (3,4,5-tribromothiophen-2-yl)-oxo-acetic acid ethyl ester as a yellow solid (1.5 g, 71%). MS (M+H)+: 422.55; 1H NMR (300 MHz, CDCl3) δ4.45 (2H, q, J=7.1 Hz), 1.44 (3H, t, J=7.1 Hz). 13C NMR (75 MHz, CDCl3) δ173.89, 161.64, 133.35, 124.81, 123.05, 122.54, 63.75, 14.11.

後処理

  1. customevacuated
  2. customflushed with nitrogen
  3. additionwas added anhydrous diethyl ether (12 ml)
  4. stirringStirring
  5. waitwas continued for 30 min
  6. customthe reaction mixture was quenched with 1N HCl
  7. customThe organic layer was separated
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under vacuum
  10. customPurification

出典と根拠

ORDレコード
ord-885df1cb6ab84dbcbca378dcb9067489
出典データセット
uspto-grants-2003_09
特許番号
US06613786B2

関連ノート

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