6-Bromo-2-naphthalenol → 6-((Trimethylsilyl)ethynyl)naphthalen-2-ol

HRID 1518404ノート

反応式

HRID 1518404 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[C:13]([Si:15]([CH3:18])([CH3:17])[CH3:16])#[CH:14]>C1COCC1.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>[CH3:16][Si:15]([C:13]#[C:14][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2)([CH3:18])[CH3:17]

参加物

6

反応物 2

HCID 271446-Bromo-2-naphthalenolHCID 66111Trimethylsilylacetylene

生成物 1

HCID 594475526-((Trimethylsilyl)ethynyl)naphthalen-2-ol

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 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a mixture of 6-bromonaphthalen-2-ol (3.8 g, 17.04 mmol), ethynyltrimethylsilane (7.08 ml, 51.1 mmol), (PPh3)2PdCl2 (1.79 g, 2.56 mmol), TEA (12 ml, 85 mmol) in THF (12 ml) was added copper(I) iodide (0.324 g, 1.70 mmol). The resulting mixture was heated at 70° C. in oil bath overnight and cooled. To the mixture was added silica gel (40 g) and the resulting mixture was dried on vacuum. The gel powder was loaded on a silica gel column, eluted with DCM to provide compound 110A.

後処理

  1. temperaturecooled
  2. additionTo the mixture was added silica gel (40 g)
  3. customthe resulting mixture was dried on vacuum
  4. washeluted with DCM

出典と根拠

ORDレコード
ord-a5a68b2d6ef343dd88b4e2c03ae494a5
出典データセット
uspto-grants-2012_07
特許番号
US08232273B2

反応ノート

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