Sodium Carbonate → 4-{Cycloheptylidene[4-(2-furanyl)phenyl]methyl}phenol

HRID 229269Notes

Reaction equation

HRID 229269 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:16]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1COCC1.O>CCOCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:16]1(=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:24]3[O:23][CH:27]=[CH:26][CH:25]=3)=[CH:3][CH:4]=2)[C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2734357Furan-2-boronic acidHCID 21881883Oxolane--water (1/1)HCID 686541254-[(4-Bromophenyl)(cycloheptylidene)methyl]phenol

Product 1

HCID 113139484-{Cycloheptylidene[4-(2-furanyl)phenyl]methyl}phenolYield 44%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

The round-bottom flask was charged with 4-[(4-bromophenyl)(cycloheptylidene)methyl]phenol (9) (0.100 g, 0.28 mmol), PdCl2(PPh3)2, (0.020 g, 0.028 mmol), 2-furanylboronic acid (0.063 g, 0.56 mmol), aqueous 2 M Na2CO3, (0.06 g, 0.56 mmol), and THF/H2O mixture (4:1, 5 mL) under a nitrogen atmosphere. The reaction mixture was refluxed for 10 h. Reaction mixture was cooled to room temperature, diluted with Et2O (10 mL) and filtered. The filtrate was diluted with EtOAc (30 mL), washed with brine, dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by silica gel chromatography using hexanes: EtOAc (19:1 to 4:1) as an eluent to give 0.0.42 g (44%) of compound 202 as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 9.28 (s, 1H), 7.70 (br s, 1H), 7.59 (d, J=6.0 Hz, 2H), 7.12 (d, J=6.0 Hz, 2H), 6.91 (d, J=6.3 Hz, 2H), 6.86 (d, J=2.4 Hz, 1H), 6.66 (d, J=6.3 Hz, 1H), 6.55 (br s, 1H), 2.37 (br s, 4H), 1.62 (br s, 8H). LCMS (ESI): m/z 343 (M−H)−.

Workup

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. customReaction mixture
  3. filtrationfiltered
  4. additionThe filtrate was diluted with EtOAc (30 mL)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude product
  9. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3af2f1fb2a49478785390979bed29cb7
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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