7-Bromo-3-methylnaphthalen-1-ol → 1-Naphthol, 3-methyl-

HRID 926203

反応式

HRID 926203 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:13])[CH:8]=[C:9]2[OH:12])=[CH:4][CH:3]=1>[Pd].CCO>[CH3:13][C:7]1[CH:8]=[C:9]([OH:12])[C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[CH:2][CH:11]=2

参加物

4

反応物 1

HCID 671262827-Bromo-3-methylnaphthalen-1-ol

生成物 1

HCID 261351-Naphthol, 3-methyl-

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
23 °C

実験手順

A slurry of 7-bromo-3-methylnaphthalen-1-ol (100 mg, 0.421 mmol), 10% w/w Pd/C (45 mg, 42.1 μmol Pd), and absolute EtOH (2.0 mL) was purged under vacuum and backfilled with H2 from a balloon several times. The suspension was stirred under a balloon of H2 at 23° C. overnight. The reaction was filtered over Celite, the cake was washed with EtOAc. The filtrate was concentrated and dissolved in DCM. The solution was loaded onto a 12 g “gold” ISCO silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product. 1H NMR (400 MHz, CDCl3) δ 8.10 (d, J=7.8 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.47-7.39 (m, 2H), 7.22 (s, 1H), 6.67 (s, 1H), 2.45 (s, 3H).

後処理

  1. filtrationThe reaction was filtered over Celite
  2. washthe cake was washed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutiondissolved in DCM
  5. custompurified by flash chromatography (ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-3ce10ff026c24790bc283c48f3f74460
出典データセット
uspto-grants-2016_03
特許番号
US09284323B2

関連ノート

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