Water → 3-(3-(Benzyloxy)-6-chloropyridin-2-yl)prop-2-yn-1-ol

HRID 1776898ノート

反応式

HRID 1776898 の反応式
[CH2:1]([O:8][C:9]1[C:10](I)=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([OH:20])[C:18]#[CH:19].O>CCN(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:1]([O:8][C:9]1[C:10]([C:19]#[C:18][CH2:17][OH:20])=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 962WaterHCID 7859Propargyl alcoholHCID 587310103-(Benzyloxy)-6-chloro-2-iodopyridine

生成物 1

HCID 867282833-(3-(Benzyloxy)-6-chloropyridin-2-yl)prop-2-yn-1-ol収率 91.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

A mixture of compound 3-(benzyloxy)-6-chloro-2-iodopyridine (2.5 g, 7.2 mmol), prop-2-yn-1-ol (443 mg, 7.9 mmol), Pd(PPh3)2Cl2 (280 mg, 0.4 mmol) and CuI (76 mg, 0.4 mmol) in Et3N (25 mL) was stirred at room temperature for 6 hours. Water (50 mL) was added and the mixture was extracted with dichloromethane. The organic layer was washed with brine and dried over Na2SO4. After concentrated, the resulting residue was purified using column chromatography (petroleum ether:ethyl acetate=2:1) to provide the product of compound 3-(3-(benzyloxy)-6-chloropyridin-2-yl)prop-2-yn-1-ol (1.8 g, yield: 90%). 1H-NMR (CDCl3, 400 MHz) δ 7.42˜7.33 (m, 5H), 7.17 (s, 2H), 5.18 (s, 2H), 4.54 (s, 2H). MS (M+H)+: 274/276.

後処理

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated
  5. customthe resulting residue was purified

出典と根拠

ORDレコード
ord-68abb589bdcb4926ac0829e6e047f236
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

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