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

HRID 1049622

Reaction equation

HRID 1049622 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-d605d5ded35a41ffab5dceefbd1d25c7
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Linked notes

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