Lithium diisopropylamide → HCID 22490963、化合物

HRID 2180599ノート

反応式

HRID 2180599 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])[CH3:18])[C:3]=1[O:20][CH2:21][CH3:22].[CH:23]([N-]C(C)C)(C)C.[Li+]>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])[CH2:18][CH3:23])[C:3]=1[O:20][CH2:21][CH3:22]

参加物

4

反応物 2

HCID 2724682Lithium diisopropylamideHCID 22490930HCID 22490930、化合物

生成物 1

HCID 22490963HCID 22490963、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, 1.75 g, 4.81 mmol) in THF (33 mL) at −78° C. was added lithium diisopropylamide (1.5 M in cyclohexane, 3.85 mL, 5.78 mmol). The bath was removed and the mixture was stirred for 2.5 h. The mixture was cooled to −78° C. again and methyl iodide was added. The mixture was stirred at room temperature for 16 h, quenched with saturated ammonium chloride, and 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 (normal phase, 2% ethyl acetate in hexanes) to give the title compound as clear oil.

後処理

  1. customThe bath was removed
  2. additionmethyl iodide was added
  3. stirringThe mixture was stirred at room temperature for 16 h
  4. customquenched with saturated ammonium chloride
  5. extractionextracted with diethyl ether
  6. washThe combined ethereal layers were washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. 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-87e9310f14634225a98a2a9c6779e55c
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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