Sulfoxonium, trimethyl-, iodide (1:1) → Ethyl 1-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)cyclopropanecarboxylate

HRID 527564ノート

反応式

HRID 527564 の反応式
[I-].[CH3:2][S+](C)(C)=O.[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][O:19][CH3:20])[C:12]=1[C:21](=[CH2:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CS(C)=O>[CH3:20][O:19][CH2:18][O:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH2:9][O:8][CH3:7])[C:12]=1[C:21]1([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:2][CH2:27]1

参加物

4

反応物 2

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 67235183Ethyl 2-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-2-propenoate2 回

生成物 1

HCID 67235562Ethyl 1-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)cyclopropanecarboxylate収率 80.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

To a solution of trimethylsulfoxonium iodide (1.805 g, 8.20 mmol) in dry dimethyl sulfoxide (20 mL) sodium hydride 60% dispersion in mineral oil (0.310 g, 7.75 mmol) was added and the reaction mixture was stirred for 1 hour at room temperature. A solution of ethyl 2-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-2-propenoate (Intermediate 81, 1.35 g) in dry dimethyl sulfoxide (10 mL) was slowly added and the reaction mixture was stirred for 1 hour at room temperature. The reaction was quenched with an aqueous saturated solution of ammonium chloride (10 ml), diluted with water (20 ml) and extracted with ethyl acetate (2×50 ml). The organic layer was washed with water (50 ml), dried over sodium sulphate, filtered and evaporated. The residue was purified by flash chromatography (Biotage system) on silica gel using a 50 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 8:2 as eluents affording the title as a colourless oil (1.14 g).

後処理

  1. stirringthe reaction mixture was stirred for 1 hour at room temperature
  2. customThe reaction was quenched with an aqueous saturated solution of ammonium chloride (10 ml)
  3. additiondiluted with water (20 ml)
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe organic layer was washed with water (50 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (Biotage system) on silica gel using a 50 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 8:2 as eluents

出典と根拠

ORDレコード
ord-8b0c4b7b852f4dd1879360632acb1a26
出典データセット
uspto-grants-2016_05
特許番号
US09346790B2

反応ノート

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