Dimethylformamide → HCID 86760729, compound

HRID 2113665Notes

Reaction equation

HRID 2113665 reaction equation
Br[C:2]1[C:3](=O)C[C:5]2([CH2:20]CCC)[CH2:14][CH2:13][C:12]3[C:7](=CC=[C:10]([O:16][CH2:17][O:18][CH3:19])[C:11]=3Br)[C:6]=12.[Cl-].[Li+].[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:32]=CC=C[CH:28]=1.C[Sn](C)(C)C.CN(C)[CH:53]=[O:54]>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>[CH3:19][O:18][CH2:17][O:16][CH:10]1[CH:11]2[CH2:12][CH2:7][C:6]3[C:2]([C:28]2=[C:27]([CH3:32])[C:53]1=[O:54])=[CH:3][CH:13]=[CH:14][C:5]=3[CH3:20]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 11661TetramethyltinHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 58604072HCID 58604072, compound

Product 1

HCID 86760729HCID 86760729, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 1,6-dibromo-3a-butyl-7-(methoxymethoxy)-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one (139 mg, 0.30 mmol), dichlorobis(triphenylphosphine)palladium(II) (23 mg, 0.03 mmol), lithium chloride (25 mg, 0.60 mmol), triphenylphosphine (16 mg, 0.06 mmol), and anhydrous N,N-dimethylformamide (DMF, 0.6 mL) was purged with N2 and treated with tetramethyltin (0.416 mL, 3.0 mmol). The mixture was stirred under a N2 atmosphere and heated at 100° C. for 22 hours. After cooling, the mixture was concentrated under vacuum, the residue was diluted with EtOAc and filtered through a pad of silica gel, and the filtrate was evaporated under vacuum to provide an oil. The crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 12S (1.2×7.5 cm) silica gel column, eluting with 10:1 hexane-EtOAc (50 mL) followed by 4:1 hexane-EtOAc (100 mL). The product-containing fractions were evaporated under vacuum to afford 3a-butyl-7-(methoxymethoxy-1,6-dimethyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one as an oil.

Workup

  1. customwas purged with N2
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under vacuum
  4. additionthe residue was diluted with EtOAc
  5. filtrationfiltered through a pad of silica gel
  6. customthe filtrate was evaporated under vacuum
  7. customto provide an oil
  8. customThe crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 12S (1.2×7.5 cm) silica gel column
  9. washeluting with 10:1 hexane-EtOAc (50 mL)
  10. customThe product-containing fractions were evaporated under vacuum

Sources & evidence

ORD record
ord-db26a632c31e4ec9b60573934025dde5
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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