1,2-Dimethoxyethane → 4-{Cycloheptylidene[4-(3-furanyl)phenyl]methyl}phenol

HRID 2100167Notes

Reaction equation

HRID 2100167 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][C:25](B(O)O)=[CH:24]1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>CCOCC.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:16]1(=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:25]3[CH:26]=[CH:27][O:23][CH:24]=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 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 686541254-[(4-Bromophenyl)(cycloheptylidene)methyl]phenol

Product 1

HCID 112908874-{Cycloheptylidene[4-(3-furanyl)phenyl]methyl}phenolYield 92%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A round-bottom flash was charged with 4-[(4-bromophenyl)(cycloheptylidene)methyl]phenol (200) (1.0 g, 2.8 mmol), Pd(PPh3)4, (0.323 g, 0.28 mmol), 3-furanylboronic acid (0.627 g, 5.6 mmol), aqueous 2 M Na2CO3, (1.2 g, 4.7 mL, 11.2 mmol), and DME (15 mL) under a nitrogen atmosphere. The reaction mixture was refluxed for 5 h. Reaction mixture was cooled at room temperature, diluted with Et2O (30 ml) and filtered. The filtrate was diluted with EtOAc (100 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 n-hexanes:EtOAc (19:1 to 4:1) as an eluent to give 0.887 g (92%) of the title compound 201 as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.73 (s, 1H), 7.48 (t, J=1.5 Hz, 1H), 7.42 (d, J=8.1 Hz, 2H), 7.18 (d, J=8.1 Hz, 2H), 7.07 (d, J=8.4 Hz, 2H), 6.77 (d, J=8.4 Hz, 1H), 6.70 (d, J=1.2 Hz, 1H), 2.37 (br s, 4H), 1.62 (br s, 8H). LCMS (ESI): m/z 343 (M−H)−. Anal. Calcd for C24H24O2, C, 83.69; H, 7.02; Found: C, 82.69; H, 7.06.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customReaction mixture
  3. filtrationfiltered
  4. additionThe filtrate was diluted with EtOAc (100 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-f2f06a758d4e46f9a438e9617f198db0
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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