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

HRID 527564노트

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HRID 527564 반응식
[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

참가 물질

4

반응물 2

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 67235183Ethyl 2-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-2-propenoate2회

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8b0c4b7b852f4dd1879360632acb1a26
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346790B2

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