Methanesulfonic Acid → 2-Dipropylamino-8-methylsulfinyl-1,2,3,4-tetrahydronaphthalene

HRID 256565

반응식

HRID 256565 반응식
[CH3:1][S:2]([OH:5])(=O)=O.[CH2:6]([N:9]([CH2:22][CH2:23][CH3:24])[CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[C:13](SC)[CH:14]=[CH:15][CH:16]=2)[CH2:11]1)[CH2:7][CH3:8].I([O-])(=O)(=O)=O.[Na+].[NH4+].[OH-]>O>[CH2:22]([N:9]([CH2:6][CH2:7][CH3:8])[CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[C:13]([S:2]([CH3:1])=[O:5])[CH:14]=[CH:15][CH:16]=2)[CH2:11]1)[CH2:23][CH3:24]

참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 14923Ammonium HydroxideHCID 99037352-Dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthaleneHCID 23667635Sodium periodate

생성물 1

HCID 190432102-Dipropylamino-8-methylsulfinyl-1,2,3,4-tetrahydronaphthalene수율 85%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To a solution of water (60 mL) which contains methanesulfonic acid (0.16 mL, 2.33 mMol) was added 2-dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthalene (630 mg, 2.33 mMol). To this solution was added a solution of sodium metaperiodate (550 mg, 2.57 mMol) in water (10 mL), and the reaction mixture was stirred for two days at room temperature. The reaction mixture was made basic (NH4OH) and extracted with dichloromethane. The organic extracts were combined, dried (Na2SO4) and concentrated in vacuo to give the crude title compound as a light yellow oil. Purification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH) gave the desired product (580 mg, 85%) as a colorless oil. The fumarate salt was formed. Recrystallization (ethanol/diethyl ether) gave a colorless, crystalline solid which was found to be extremely hygroscopic. Drying in a vacuum dessicator (60° C., 18 hours) gave a colorless glass (260 mg, m.p.=63° C.).

후처리

  1. extractionextracted with dichloromethane
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto give the crude title compound as a light yellow oil
  5. customPurification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH)

출처 및 근거

ORD 기록
ord-6677ddd6dedc4a5fa5b5013fa9e77b30
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258379

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