Hexane → 2-Dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthalene

HRID 256564

反応式

HRID 256564 の反応式
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2.C([Li])CCC.CCCCCC.[CH3:30][S:31]SC>O1CCCC1.O>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([S:31][CH3:30])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH3:15]

参加物

7

反応物 4

HCID 8058HexaneHCID 12232Dimethyl DisulfideHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

生成物 1

HCID 99037352-Dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthalene収率 80.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene (600 mg, 1.93 mMol) in tetrahydrofuran (20 mL) at -78° C. was added a solution of n-butyllithium in hexane (1.6 M, 1.9 mL, 3.04 mMol). The solution was stirred at -78° C. for one hour, forming a light orange solution. Dimethyl disulfide (0.24 mL, 3.00 mMol) was added, and the reaction mixture was allowed to warm gradually to room temperature. The colorless solution was diluted with water and extracted with dichloromethane. The dichloromethane extracts were combined, dried (Na2SO4), and concentrated in vacuo to give the crude product as a light yellow oil. Purification by flash chromatography (3% methanol in dichloromethane+ tr. NH4OH) gave the product as a colorless, viscous oil (430 mg, 80%). The hydrochloride salt was formed. Recrystallization (ethanol/diethyl ether) gave a colorless, crystalline solid (m.p.=185° C.).

後処理

  1. customforming a light orange solution
  2. temperatureto warm gradually to room temperature
  3. extractionextracted with dichloromethane
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product as a light yellow oil
  7. customPurification by flash chromatography (3% methanol in dichloromethane+ tr. NH4OH)

出典と根拠

ORDレコード
ord-38b33c1164ab486990b77e9053ff4e22
出典データセット
uspto-grants-1993_11
特許番号
US05258379

関連ノート

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