Dimethyl Sulfoxide → Methane, sulfinylbis-, ion(1-), sodium

HRID 854956

反応式

HRID 854956 の反応式
[CH3:1]CCCCC.[H-].[Na+:8].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:17]([CH3:21])([CH3:20])[CH:18]=O)[CH:14]=[CH:15][CH:16]=1.[CH3:22][S:23]([CH3:25])=[O:24]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][S:23]([CH2-:25])=[O:24].[Na+:8].[CH3:20][C:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH3:9])[CH:12]=1)([CH3:21])[CH:18]=[CH2:1]

参加物

7

反応物 4

HCID 679Dimethyl Sulfoxide2 回HCID 8058HexaneHCID 24758Sodium hydrideHCID 132969932-(3-Methoxyphenyl)-2-methylpropanal

生成物 2

HCID 10154010Methane, sulfinylbis-, ion(1-), sodiumHCID 132969951-(1,1-Dimethylprop-2-enyl)-3-methoxybenzene

試薬・触媒・溶媒 1

HCID 74505Methyltriphenyliphosphonium bromide触媒

反応条件

温度
60 °C

実験手順

A solution of sodium dimsylate was prepared by dissolving hexane washed 60% NaH (4.89 g, 122 mmoles) in mineral oil in 120 mL of DMSO with heating to 60° C. To 40 mL of this solution added methyltriphenylphosphonium bromide (14.5 g, 40.7 mmoles) of as a solid, forming a thick paste. A solution of 2-(3-methoxyphenyl)-2-methylpropanal (5.00 g, 28.1 mmoles) in 6 mL of DMSO was added, and the mixture stirred overnight. The mixture was partitioned between Et2O and water, and the aqueous layer further extracted with Et2O. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated. Chromatography of the residue over silica gel using DCM as eluent gave 1-(1,1-dimethylprop-2-enyl)-3-methoxybenzene, 4.25 g, as an oil.

後処理

  1. customforming a thick paste
  2. customThe mixture was partitioned between Et2O and water
  3. extractionthe aqueous layer further extracted with Et2O
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-e8c2f21d9c0f4562bb95578756d53a1e
出典データセット
uspto-grants-2007_08
特許番号
US07259266B2

関連ノート

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