Triphenylphosphine → 3,4-dihydro-6-methylnaphthalen-1(2H)-one

HRID 1049622

반응식

HRID 1049622 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[CH3:13]B(O)O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:13][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 101050696-Bromo-1-tetralone

생성물 1

HCID 1626203,4-dihydro-6-methylnaphthalen-1(2H)-one수율 88%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 19 (1.4 g, 6.1 mmol), methyl boronic acid (0.6 g, 9.3 mmol), Pd(OAc)2 (0.07 g, 0.31 mmol), PPh3 (0.16 g, 0.61 mmol), and K3PO4 (5.2 g, 24 mmol) in dry THF were stirred at reflux under N2 atm overnight. After cooling at room temperature, crude was filtered through celite, concentrated by rotary evaporation, and purified by column chromatography to give 6-methyl-3,4-dihydronaphthalen-1(2H)-one (20) (88%). 1H NMR (600 MHz, CDCl3) δ 7.93 (d, J=12.0 Hz, 1H), 7.11 (d, J=12.0 Hz, 1H), 7.06 (s, 1H), 2.92 (t, J=6.0 Hz, 2H), 2.63 (t, J=12.0 Hz, 2H), 2.37 (s, 3H), 2.13-2.10 (m, 2H). GC-MS (ES) for C11H12O [M]+ 160.

후처리

  1. temperatureat reflux under N2 atm overnight
  2. filtrationcrude was filtered through celite
  3. concentrationconcentrated by rotary evaporation
  4. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-d605d5ded35a41ffab5dceefbd1d25c7
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382245B2

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