Methanol → 2-chloro-1-((E)-2-methanesulfinyl-2-methylsulfanyl-vinyl)-3-methoxy-benzene

HRID 1773976ノート

反応式

HRID 1773976 の反応式
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C[CH:13]([S:17][CH:18](S(C)=O)C)[S:14]([CH3:16])=[O:15].CO>C1COCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[C:13](/[S:14]([CH3:16])=[O:15])\[S:17][CH3:18]

参加物

6

反応物 3

HCID 887MethanolHCID 125756952-Chloro-3-methoxybenzaldehydeHCID 54140058Methylmethylsulfinylmethyl sulfide

生成物 1

HCID 220378702-chloro-1-((E)-2-methanesulfinyl-2-methylsulfanyl-vinyl)-3-methoxy-benzene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 66854Benzyltrimethylammonium hydroxide溶媒

実験手順

To a solution of 2-chloro-3-methoxybenzaldehyde (1.74 g, 10.0 mmol, 1.0 eq.) and methyl(methylsulfinyl)methyl sulfide (1.72 mL, 16.1 mmol, 1.6 eq.) in THF (9 mL), benzyltrimethylammonium hydroxide solution in methanol (2.3 mL, 10.0 mmol, 1.0 eq.) was added. The resulting solution was refluxed for 18 hours. The solvent was removed in vacuo. The residue was taken up in AcOEt and washed with 1M aq. HCl soln., water, and sat. aq. NaCl soln. The org. layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane+20% AcOEt to Heptane+65% AcOEt) to yield 2-chloro-1-((E)-2-methanesulfinyl-2-methylsulfanyl-vinyl)-3-methoxy-benzene as a pale orange oil.

後処理

  1. temperatureThe resulting solution was refluxed for 18 hours
  2. customThe solvent was removed in vacuo
  3. washwashed with 1M aq. HCl soln
  4. dry with materiallayer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane+20% AcOEt to Heptane+65% AcOEt)

出典と根拠

ORDレコード
ord-8179540632984d578b36485f7a7fcce1
出典データセット
uspto-grants-2016_02
特許番号
US09255090B2

反応ノート

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