Tetrahydrofuran → (E)-3-{8-(4-fluoro-3-methylphenyl)-10,10-dimethyl-1,5dithiaspiro{5.5}undec-8-en-9-yl}propenal

HRID 359559ノート

反応式

HRID 359559 の反応式
[Li+].CC([N-]C(C)C)C.C(=NC1CCCCC1)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:26][C:27]3([CH2:33][C:34]([CH3:39])([CH3:38])[C:35]=2C=O)[S:32][CH2:31][CH2:30][CH2:29][S:28]3)=[CH:21][C:20]=1[CH3:40].[CH2:41]1C[O:44][CH2:43][CH2:42]1>CCOCC>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:26][C:27]3([CH2:33][C:34]([CH3:38])([CH3:39])[C:35]=2/[CH:41]=[CH:42]/[CH:43]=[O:44])[S:28][CH2:29][CH2:30][CH2:31][S:32]3)=[CH:21][C:20]=1[CH3:40]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 10964544N-cyclohexylethanimineHCID 150569548-(4-Fluoro-3-methylphenyl)-10,10-dimethyl-1,5dithiaspiro{5.5}undec-8-en-9-carboxaldehyde

生成物 1

HCID 15056955(E)-3-{8-(4-fluoro-3-methylphenyl)-10,10-dimethyl-1,5dithiaspiro{5.5}undec-8-en-9-yl}propenal

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

To a -20° C. solution of LDA (19.0 mmol) in 60 mL anhydrous THF was added ethylidenecyclohexylamine (Org. Syn. 50, 66) (2.38 gm, 19.0 mmol). The solution was stirred for 30 min, cooled to -78° C. and a solution of 8 (3.50 g, 10.0 mmol) in 60 mL was added. The mixture was stirred for 3 h, diluted with ether and quenched with H2O. The organic layer was washed with H2O and brine and dried (MgSO4). Removal of the volatiles in vacuo and purification of the residue by HPLC. using 10:1 hexanes:EtOAc provided 1.6 g of the orange color gum.

後処理

  1. stirringThe mixture was stirred for 3 h
  2. customquenched with H2O
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. customRemoval of the volatiles
  6. customin vacuo and purification of the residue by HPLC
  7. customEtOAc provided 1.6 g of the orange color gum

出典と根拠

ORDレコード
ord-69e39f5144c145e6b746ee31762868ae
出典データセット
uspto-grants-1991_03
特許番号
US05001144

反応ノート

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