Sodium Carbonate → HCID 10934165, compound

HRID 586648Notes

Reaction equation

HRID 586648 reaction equation
B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([CH3:36])([CH3:35])[CH2:30][CH2:29][C:28]2([CH3:38])[CH3:37].I/[C:40](/[CH3:44])=[CH:41]\[CH2:42][OH:43].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:35][C:31]1([CH3:36])[CH2:30][CH2:29][C:28]([CH3:38])([CH3:37])[C:27]2[CH:26]=[C:25](/[C:40](/[CH3:44])=[CH:41]\[CH2:42][OH:43])[CH:34]=[CH:33][C:32]1=2

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 2266856-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthaleneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 5314691(2Z)-3-Iodo-2-buten-1-ol

Product 1

HCID 10934165HCID 10934165, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Bis(pinacolato)diboron (5.8 g, 22.5 mmol), potassium acetate (4.5 g, 45 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium (PdCl2(dppf)2) (500 mg, 0.6 mmol) were added to a solution of Intermediate 1 (4 g, 15 mmol) in 50 mL of DMF under argon. The mixture was then stirred at 80° C. for 24 h. After cooling to room temperature, 3-iodo-but-2Z-en-1-ol (6 g, 30 mmol), 2M Na2CO3 (30 ml), and PdCl2(dppf)2 (500 mg, 0.6 mmol) were added to the mixture, which was then stirred at 80° C. for another 24 h. The reaction was finally quenched with water (20 mL) and extracted with ether (3×10 mL). The organic layer was washed with brine (2×10 mL), dried (MgSO4) and concentrated to give a crude brown oil. The crude product was purified by flash chromatography using 20% EtOAc in hexane to give the title compound (3 g, 77% yield) as a colorless oil:

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringwas then stirred at 80° C. for another 24 h
  3. customThe reaction was finally quenched with water (20 mL)
  4. extractionextracted with ether (3×10 mL)
  5. washThe organic layer was washed with brine (2×10 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a crude brown oil
  9. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ed9cfd02c4a04a5d9c7d80ee25cdbbe0
Source dataset
uspto-grants-2005_08
Patent number
US06936636B2

Reaction notes

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