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

HRID 1049622

反応式

HRID 1049622 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d605d5ded35a41ffab5dceefbd1d25c7
出典データセット
uspto-grants-2016_07
特許番号
US09382245B2

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