Methyl iodide → HCID 69732452、化合物

HRID 2180600ノート

反応式

HRID 2180600 の反応式
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=[O:19])C)[C:3]=1[O:20][CH2:21][CH3:22].C([N-][CH:27]([CH3:29])[CH3:28])(C)C.[Li+].CI>C1COCC1>[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:6]=2[CH:5]=[C:4]([C:17](=[O:19])[CH:27]([CH3:28])[CH3:29])[C:3]=1[O:20][CH2:21][CH3:22]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 22490930HCID 22490930、化合物

生成物 1

HCID 69732452HCID 69732452、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 1-(4-bromo-3-ethoxy-8-isopropyl-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-109, 512 mg, 1.4 mmol) in THF (10 mL) at −78° C. was added lithium diisopropylamide (1.5 M in cyclohexane, 2.0 mL, 3.0 mmol). The cold bath was removed and the mixture was stirred for 3 h. The mixture was cooled to −78° C. again and methyl iodide (0.52 mL, 8.34 mmol) was added. The mixture was stirred at room temperature for 16 h then quenched with ammonium chloride (sat), extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexanes) followed by HPLC (Waters-Nova Pak column, 2% ethyl acetate in hexanes) to give the title compound.

後処理

  1. customThe cold bath was removed
  2. stirringThe mixture was stirred at room temperature for 16 h
  3. customthen quenched with ammonium chloride (sat)
  4. extractionextracted with diethyl ether
  5. washThe combined ethereal layers were washed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-ac0d837ba6d14f3d99b19f3f64226412
出典データセット
uspto-grants-2005_05
特許番号
US06887896B1

反応ノート

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