Sodium Iodide → 2-Chloro-5-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxy]-6-iodomethyl-3-methoxy-benzoic acid allyl ester

HRID 1082166ノート

反応式

HRID 1082166 の反応式
[CH2:1]([O:4][C:5](=[O:27])[C:6]1[C:11]([CH:12]=O)=[C:10]([O:14][Si:15]([CH3:23])([CH3:22])[C:16]([CH3:21])([CH3:20])[CH:17]([CH3:19])[CH3:18])[CH:9]=[C:8]([O:24][CH3:25])[C:7]=1[Cl:26])[CH:2]=[CH2:3].[I-:28].[Na+].C[Si](C)(C)Cl.C[SiH2]O[Si](C)(C)C>C(#N)C>[CH2:1]([O:4][C:5](=[O:27])[C:6]1[C:11]([CH2:12][I:28])=[C:10]([O:14][Si:15]([CH3:23])([CH3:22])[C:16]([CH3:21])([CH3:20])[CH:17]([CH3:19])[CH3:18])[CH:9]=[C:8]([O:24][CH3:25])[C:7]=1[Cl:26])[CH:2]=[CH2:3]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 529377352-Chloro-5-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxy]-6-formyl-3-methoxy-benzoic acid allyl esterHCID 57376941Tetramethyl disiloxane

生成物 1

HCID 529377372-Chloro-5-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxy]-6-iodomethyl-3-methoxy-benzoic acid allyl ester収率 80.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
20 °C

実験手順

To a solution of 3.3 g of 2-chloro-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-formyl-3-methoxy-benzoic acid allyl ester in 4 ml of acetonitrile were added 1.8 g of sodium iodide and 1.6 ml of trimethyl-chlorosilane. A white precipitate occurred. The mixture was stirred for 5 min at 20° C. The suspension was cooled to 0° C. and 1.48 ml of tetramethyldisiloxane were added. The mixture was stirred for hours at 0° C. and then partitioned between 20 ml of ethyl acetate and 20 ml of water. The aqueous phase was extracted twice with 20 ml of ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was chromatographed on silica gel using diethyl ether/hexane (3:1, v/v) as eluent to afford 3.39 g of 2-chloro-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-iodomethyl-3-methoxy-benzoic acid allyl ester as a colorless oil.

後処理

  1. temperatureThe suspension was cooled to 0° C.
  2. stirringThe mixture was stirred for hours at 0° C.
  3. custompartitioned between 20 ml of ethyl acetate and 20 ml of water
  4. extractionThe aqueous phase was extracted twice with 20 ml of ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-1d8872e3bc3146a292a8ffbe7fc62c6f
出典データセット
uspto-grants-1996_12
特許番号
US05589473

反応ノート

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