Diethyl Ether → 3,4-Dihydro-4,4-dimethyl-6-acetyl-1-(1,1-dimethlethyl)naphthalene

HRID 24585

反応式

HRID 24585 の反応式
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=O)[CH2:4][CH2:3]1.[Li][C:15]([CH3:18])([CH3:17])[CH3:16].O=S(Cl)Cl.[CH3:23][CH2:24][O:25]CC>>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:24](=[O:25])[CH3:23])[CH:10]=2)[C:5]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH2:3]1

参加物

5

反応物 4

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-oneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 225715533,4-Dihydro-4,4-dimethyl-6-acetyl-1-(1,1-dimethlethyl)naphthalene

反応条件

温度
-78 °C

実験手順

To a solution of 6-(2-methyl-1,3-dioxolan-2-yl)]-3,4-dihydro-4,4-dimethylnaphthlen-1(2H)-one ((Compound D1S, 353 mg, 1.36 mmol) in 3 ml of dry ether at −78° C. was added dropwise t-BuLi (1 ml, 1.7 mmol, 1.7 M solution in pentane). This clear light yellow solution was left at −78° C. for 30 min. Then, freshly distilled SOCl2 (0.15 ml, 2.0 mmol) was added. The reaction mixture was stirred at −78° C. for additional 30 min and thereafter slowly warmed to room temperature. The reaction was quenched by addition of saturated NH4Cl. The white solids were removed by filtration and the clear solution was concentrated to an oil, and purified by column chromatography with ethyl acetate/hexane (1/10) to give the title compound as a yellow oil.

後処理

  1. temperatureslowly warmed to room temperature
  2. customThe reaction was quenched by addition of saturated NH4Cl
  3. customThe white solids were removed by filtration
  4. concentrationthe clear solution was concentrated to an oil
  5. custompurified by column chromatography with ethyl acetate/hexane (1/10)

出典と根拠

ORDレコード
ord-20e1168c6e1b4640856350a8323c568b
出典データセット
uspto-grants-2005_02
特許番号
US06855832B2

関連ノート

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