Sodium Hydroxide → 1-(2,6-Dimethoxyphenyl)naphthalene

HRID 54027

反応式

HRID 54027 の反応式
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][CH3:11].[C:12]1(OB(O)O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]1([C:2]2[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=2[O:10][CH3:11])[C:21]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 6122962-Bromo-1,3-dimethoxybenzeneHCID 13862914Naphthylboric acid

生成物 1

HCID 154981511-(2,6-Dimethoxyphenyl)naphthalene収率 78.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 1-bromo-2,6-dimethoxybenzene, (2.63 g, 12.1 mmol), tetrakis(triphenylphosphine)palladium (0) (0.91 g, 0.76 mol) and 1-naphthylboric acid (4.16 g, 23.9 mmol) in 1,4-dioxane (160 ml), a 2N aqueous solution of sodium hydroxide (13 ml) was added, and the mixture was heated to reflux. After cooling, the solvent was evaporated off, and the residue was dissolved in diethyl ether. The diethyl ether solution was washed with water and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated off, and the residue was purified by silica gel column chromatography (developing phase: n-hexane/ethyl acetate=5/1) to obtain 1-naphthyl-2,6-dimethoxybenzene (2.50 g).

後処理

  1. temperaturethe mixture was heated to reflux
  2. temperatureAfter cooling
  3. customthe solvent was evaporated off
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washThe diethyl ether solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThen, the solvent was evaporated off
  8. customthe residue was purified by silica gel column chromatography (developing phase: n-hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-0aae8bddb0dc42ebbc926bf057bf5887
出典データセット
uspto-grants-1997_04
特許番号
US05621129

関連ノート

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