Sodium Carbonate → 7-(m-Tolyl)chroman-4-one

HRID 63622

反応式

HRID 63622 の反応式
Br[C:2]1C=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[CH3:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=[O:24].[Na+].[Na+]>O1CCOCC1.O.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>[CH3:13][C:14]1[CH:15]=[C:16]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[O:24])[CH2:5][CH2:6][O:7][C:8]=3[CH:12]=2)[CH:17]=[CH:18][CH:19]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 101050696-Bromo-1-tetralone

生成物 1

HCID 1185977737-(m-Tolyl)chroman-4-one収率 96%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a suspension of 6-bromo-1,2,3,4-tetrahydronaphthalen-1-one (2.0 g, 8.9 mmol), 3-methylbenzeneboronic acid (1.8 g, 13.2 mmol), Na2CO3 (2.8 g, 26.4 mmol) in dioxane (40 mL) and water (2 mL) was added Pd(PPh3)4 (509 mg, 0.4 mmol) at rt under N2. The reaction was stirred at 100° C. overnight. The reaction was filtered and concentrated. Purification by silica gel chromatography (PE:EtOAc=12:1) gave 2.0 g (96%) of the title compound as a white oil. 1H NMR (300 MHz, CDCl3): δ 2.44 (3H, s), 2.86 (2H, t, J=6.6 Hz), 4.59 (2H, t, J=6.6 Hz), 7.20-7.29 (3H, m), 7.36-7.44 (3H, m), 7.87 (1H, d, J=8.1 Hz). [M+H] Calc'd for C16H14O2, 239. Found, 239.

後処理

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (PE:EtOAc=12:1)

出典と根拠

ORDレコード
ord-bb3e3bb2807d4c2a8790f530ae895f35
出典データセット
uspto-grants-2016_09
特許番号
US09447046B2

関連ノート

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