Sodium Carbonate → 7-Phenylisochroman-4-one

HRID 22271Notes

Reaction equation

HRID 22271 reaction equation
[C:1]1(OB(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11](=[O:14])([O-])[O-].[Na+].[Na+].[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:24]([OH:26])C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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>[C:1]1([C:21]2[CH:22]=[C:17]3[C:18]([C:11](=[O:14])[CH2:24][O:26][CH2:23]3)=[CH:19][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 21863594Toluene ethanol

Product 1

HCID 186867407-Phenylisochroman-4-oneYield 70%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

Nitrogen gas was bubbled through a mixture of the product of part e (0.611 g, 27 mmol) and phenylboric acid (0.36 g, 29 mmol) in 5:2 toluene/ethanol(30 mL) for 4 hours. Sodium carbonate (0.57 g, 5.38 mmol) was added followed by tetrabutylammonium bromide (0.049 g, 0.13 mmol) and tetrakis(triphenylphosphine)palladium (0.012 g, 0.04 mmol). The solution was heated at reflux for 18 h, cooled to room temperature, and evaporated. The residue was taken up in water (50 mL) and extracted with ethyl acetate (3×20 mL). The organics were combined, washed with brine, dried and evaporated. The solid was recrystallized from hexane to provide 0.429 g (70%) of 7-phenylisochroman-4-one as a gold-colored solid, mp 127°-128° C.: 1H NMR (CDCl3) δ8.12 (d, 1H), 7.60-7.66 (m, 3H), 7.39-7.51 (m, 4H), 4.96 (s, 2 H), 4.41 (s, 2H); IR (KBr) 1688 cm-1 ; Mass spectrum m/z=225 (M+H); Anal. calcd. for C15H12O2 : C 80.34, H 5.39; Found: C 80.03, H 5.45.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 18 h
  3. customevaporated
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. washwashed with brine
  6. customdried
  7. customevaporated
  8. customThe solid was recrystallized from hexane

Sources & evidence

ORD record
ord-279e2ce874524bb798c8e2a40a5e5657
Source dataset
uspto-grants-1995_06
Patent number
US05428040

Reaction notes

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