Allyl bromide → Allyl tritylsulfide

HRID 446690

반응식

HRID 446690 반응식
[Na].[C:2]1([C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[SH:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](Br)[CH:23]=[CH2:24]>CO>[CH2:24]([S:9][C:8]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:23]=[CH2:22]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 5360545Sodium2회

생성물 1

HCID 637326Allyl tritylsulfide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Initially, sodium (2 g) was added to 200 mL MeOH in a reflux apparatus, stirred until the sodium was dissolved, and then 25 g of triphenylmethanethiol (TrSH) was added. The reaction mixture was refluxed for 1 hour, 10 mL allyl bromide was then added, and the mixture was refluxed for another 2 hours. The solution was allowed to cool, 19 g of particulate material, trityl allyl sulfide (TrSAll), was obtained by filtration using filter paper, and it was used directly for the next step without any purification. tert-BuOK (11 g) was added to a solution of 19 g of TrSAll in 100 mL anhydrous tetrahydrofuran (THF) and 200 mL tert-BuOH, and the reaction mixture was stirred at 20-22° C. overnight. The solvent in the reaction mixture was removed by rotary evaporation, water and CH2Cl2 was added to the residue, and the product was extracted into the CH2Cl2 phase. Trityl 1-propenyl sulfide (TrSPe) was obtained as a white color powder by purification of the CH2Cl2 extract on a silica gel column eluted with 10% CH2Cl2 in hexane.

후처리

  1. dissolutionwas dissolved
  2. temperatureThe reaction mixture was refluxed for 1 hour
  3. temperaturethe mixture was refluxed for another 2 hours
  4. temperatureto cool

출처 및 근거

ORD 기록
ord-4015ee71b56b479d9aae85599d3880fc
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481284B2

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