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Methyl iodide → HCID 19974930、化合物

HRID 1451523
ノート
印刷プレビュー

反応式

HRID 1451523 の反応式
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[C:8]2[CH3:25])=[CH:4][CH:3]=1.[Li+].[CH3:29]C([N-]C(C)C)C.IC>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C:19]([CH3:29])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[C:8]2[CH3:25])=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 19974940HCID 19974940、化合物

生成物 1

HCID 19974930HCID 19974930、化合物収率 67.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
0 °C

実験手順

To a -78° C. solution of the ester from Step 1 (35 mg, 0.08 mmol) in 3 mL THF was added LDA (1.5M in cyclohexane, 0.1 mL, 0.15 mmol), and the solution was stirred for 30 min. A solution of iodomethane (0.1 mL, 1.6 mmol) in 1 mL HMPA was then added by syringe. The solution was stirred 15 min at -78° C., then warmed to 0° C. and quenched with saturated NH4Cl. The mixture was partitioned between ether and water and the organic layer was washed with water and brine and dried over MgSO4. The residue was purified by flash chromatography (15% ethyl acetate/hexanes) to provide 24 mg of the title compound.

後処理

  1. stirringThe solution was stirred 15 min at -78° C.
  2. customquenched with saturated NH4Cl
  3. customThe mixture was partitioned between ether and water
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customThe residue was purified by flash chromatography (15% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-6d84c1163068405bbbf7679acc31daea
出典データセット
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05604253

反応ノート

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