HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Carbonate → 4-[[4-(3-Furanyl)phenyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

HRID 1716144
Notes
Print preview

Reaction equation

HRID 1716144 reaction equation
CS(C1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[C:25]3[CH2:30][C:29]([CH3:32])([CH3:31])[CH2:28][C:27]([CH3:34])([CH3:33])[CH2:26]3)[C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[CH:7]C=1)(=O)=O.BrC1C=CC(C(=C2CC(C)(C)CC(C)(C)C2)C2C=CC([OH:49])=CC=2)=CC=1.O1C=CC(B(O)O)=C1.C([O-])([O-])=O.[Na+].[Na+]>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.O.C1COCC1>[O:49]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[C:25]3[CH2:30][C:29]([CH3:32])([CH3:31])[CH2:28][C:27]([CH3:33])([CH3:34])[CH2:26]3)[C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[CH:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 111557414-[[4'-(Methylsulfonyl)-4-biphenylyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenolHCID 686543984-[(4-Bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Product 1

HCID 577572184-[[4-(3-Furanyl)phenyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenol
Yield 69%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The Suzuki protocol described for (163) was employed. A round-bottomed flask was charged with 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (0.270 g, 0.676 mmol), PdCl2(PPh3)2 (0.048 g, 0.068 mmol), 3-furanylboronic acid (0.152 g, 1.35 mmol), aqueous 2 M Na2CO3 (1.4 mL, 0.144 g, 1.35 mmol) solution, and 4:1 THF:H2O mixture (10 mL) under a nitrogen atmosphere. The reaction mixture was refluxed for 6 h. Reaction mixture was cooled to room temperature, diluted with Et2O (10 mL) and filtered. The filtrate was diluted with EtOAc (60 mL), washed with brine, dried (Na2SO4), and concentrated under reduced pressure to afford the crude product. The product was purified by SiO2 chromatography using hexanes:EtOAc (19:1 to 4:1) as an eluent to give 0.180 g (69%) of the title compound (234) as white solid. mp 128° C.-129° C. 1H NMR (400 MHz, CDCl3): δ 7.71 (s, 1H), 7.45 (s, 1H), 7.39 (d, J=8.0 Hz, 2H), 7.16 (d, J=8.0 Hz, 2H), 7.05 (d, J=8.4 Hz, 2H), 6.74 (d, J=8.4 Hz, 2H), 6.68 (br s, 1H), 4.66 (s, 1H), 2.00 (s, 2H), 1.99 (s, 2H), 1.29 (s, 2H), 0.94 (s, 12H). LCMS (ESI): m/z 385.31 (M−H)−.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customReaction mixture
  3. filtrationfiltered
  4. additionThe filtrate was diluted with EtOAc (60 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 SiO2 chromatography

Sources & evidence

ORD record
ord-23fabfebb6c746bdb96bbf581c22eb8b
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07799828B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes