Methyl iodide → Methyl 2-(pyridin-2-yl)propanoate

HRID 2203305ノート

反応式

HRID 2203305 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[Li+].[CH3:13][Si]([N-][Si](C)(C)C)(C)C.IC>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([CH3:13])[C:8]([O:10][CH3:11])=[O:9]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 74264Methyl 2-pyridylacetateHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 54595201Methyl 2-(pyridin-2-yl)propanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Methyl 2-pyridylacetate (6.81 mL, 50 mmol) was added dropwise to LHMDS (1.0M in THF, 50 mL) and THF (65 mL) cooled to 0° C. After 30 minutes iodomethane (3.97 g, 63.5 mmol) was added to the solution. After stirring for 1 hour at 0° C. the solution was concentrated and the residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR (400 MHz, CHCl3-d): δ 8.56 (d, J=4.9 Hz, 1H); 7.66 (td, J=7.6, 1.8 Hz, 1H); 7.18 (dd, J=7.6, 4.9 Hz, 1H); 3.96 (q, J=7.2 Hz, 1H); 3.69 (s, 3H). 1.56 (d, J=7.2 Hz, 3H). m/z 166.5 (M+H).

後処理

  1. concentrationwas concentrated
  2. customthe residue was purified by silica gel chromatography
  3. customto give the indicated product

出典と根拠

ORDレコード
ord-7037350d604b4e7099140fd7087e4c6e
出典データセット
uspto-grants-2016_06
特許番号
US09365574B2

反応ノート

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