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

HRID 63622

반응식

HRID 63622 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 1185977737-(m-Tolyl)chroman-4-one수율 96%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-bb3e3bb2807d4c2a8790f530ae895f35
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447046B2

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