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

HRID 233804ノート

反応式

HRID 233804 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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.).

後処理

  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)

出典と根拠

ORDレコード
ord-95d28d1eddc741f6ad7cd7d5e514d86f
出典データセット
uspto-grants-1997_01
特許番号
US05594025

反応ノート

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