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

HRID 854956

반응식

HRID 854956 반응식
[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]

참가 물질

7

반응물 4

HCID 679Dimethyl Sulfoxide2회HCID 8058HexaneHCID 24758Sodium hydrideHCID 132969932-(3-Methoxyphenyl)-2-methylpropanal

생성물 2

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

시약·촉매·용매 1

HCID 74505Methyltriphenyliphosphonium bromide촉매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8c2f21d9c0f4562bb95578756d53a1e
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259266B2

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