Water → HCID 58604064, compound

HRID 2113656Notes

Reaction equation

HRID 2113656 reaction equation
Br[C:2]1[C:3](=[O:19])[CH2:4][C:5]2([CH2:17][CH3:18])[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=3)[C:6]=12.[C:20]1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:21]=1.O.C([O-])([O-])=O.[Cs+].[Cs+].C(B(CC)CC)C>CN(C=O)C.O1CCCC1>[CH2:20]([C:2]1[C:3](=[O:19])[CH2:4][C:5]2([CH2:17][CH3:18])[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=3)[C:6]=12)[CH3:21]

Participants

8

Reactant 5

HCID 962WaterHCID 7357TriethylboraneHCID 10796Cesium carbonateHCID 11773TriphenylarsineHCID 586040711-bromo-3a-ethyl-7-methoxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one

Product 1

HCID 58604064HCID 58604064, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1-bromo-3a-ethyl-7-methoxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one (120 mg, 0.37 mmol) in DMF (3 mL) was treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (61 mg, 0.075 mmol), triphenylarsine (23 mg, 0.075 mmol), water (0.22 mL, 12.2 mmol), Cs2CO3 (244 mg, 0.75 mmol), and triethylborane (0.75 mL of a 1.0M solution in tetrahydrofuran, 0.75 mmol). The resulting mixture was placed under a N2 atmosphere, stirred, and heated in an oil bath at 55-65° C. for 100 minutes. After cooling, the mixture was quenched with saturated aqueous NH4Cl and diluted with CH2Cl2. The organic phase was dried over MgSO4 and filtered through a pad of silica gel, washing through with EtOAc. The filtrate was evaporated under vacuum to remove the solvents. The residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates (Analtech, Newark, Del.), developing with 4:1 hexane-EtOAc. The UV visible product band was extracted with 5% MeOH in CH2Cl2 and the extracts evaporated under vacuum to provide 1,3a-diethyl-7-methoxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one as a crystalline solid.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was quenched with saturated aqueous NH4Cl
  3. additiondiluted with CH2Cl2
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered through a pad of silica gel
  6. washwashing through with EtOAc
  7. customThe filtrate was evaporated under vacuum
  8. customto remove the solvents
  9. customThe residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates (Analtech, Newark, Del.)
  10. extractionThe UV visible product band was extracted with 5% MeOH in CH2Cl2
  11. customthe extracts evaporated under vacuum

Sources & evidence

ORD record
ord-8a7b1db5666345b5830a87a5da285f90
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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