Dimethyl Sulfoxide → 4-[3-Oxo-3-(7,8-dihydro-5-(2-thienyl)-8,8-dimethyl-2-naphthalenyl)-1-propenyl)-benzoic acid

HRID 2394199Notes

Reaction equation

HRID 2394199 reaction equation
C[C:2]1(C)[CH2:11][CH2:10]C(=O)[C:8]2[CH:7]=[C:6]([C:13]([O:15]C)=[O:14])[CH:5]=[CH:4][C:3]1=2.[C]=[O:19].Br[C:21]1[CH:30]=[C:29]2[C:24]([C:25]([CH3:33])([CH3:32])[CH2:26][CH2:27][C:28]2=O)=[CH:23][CH:22]=1.C1(P([C:57]2[CH:62]=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:63][S:64]([CH3:66])=O>[Pd+2].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CO>[O:19]=[C:10]([C:22]1[CH:21]=[CH:30][C:29]2[C:28]([C:63]3[S:64][CH:66]=[CH:62][CH:57]=3)=[CH:27][CH2:26][C:25]([CH3:33])([CH3:32])[C:24]=2[CH:23]=1)[CH:11]=[CH:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1

Participants

9

Reactant 5

HCID 679Dimethyl SulfoxideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 10681077Methyl 5,5-dimethyl-5,6 dihydro-naphthalen-8(7h)-one-2-carboxylate2×HCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2×HCID 178418416HCID 178418416, compound

Product 1

HCID 545281504-[3-Oxo-3-(7,8-dihydro-5-(2-thienyl)-8,8-dimethyl-2-naphthalenyl)-1-propenyl)-benzoic acid

Reagents, catalysts & solvents 3

HCID 21950778HCID 21950778, compoundCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

Methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate (Compound E2) A degassed (with carbonmonoxide) solution of 2-bromo-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one (Compound G), palladium(II)-bis(triphenylphosphine)chloride (277 mg, 0.4 mmol), 1,3-bis(diphenylphosphino)-propane (325 mg, 0.8 mmol), DMSO (30 mL), methanol (15 mL) and triethylamine (15 mL) was placed in an oil bath (70° C.), under carbonmonoxide atmosphere) for 16h. After dilution with water the mixture was extracted with ethyl acetate. The organic layer was washed with water, 10% HCI, saturated sodiumbicarbonate and brine. The organic layer was dried over MgSO4, and the solvent was removed by distillation. The residual crude material was purified by flash chromatography (silica, 1:4 ethyl acetate: hexane) to afford the title compound as a white solid.

Workup

  1. customwas placed in an oil bath
  2. extractionAfter dilution with water the mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water, 10% HCI, saturated sodiumbicarbonate and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was removed by distillation
  6. customThe residual crude material was purified by flash chromatography (silica, 1:4 ethyl acetate: hexane)

Sources & evidence

ORD record
ord-81d7654e7d6a4a09a7a00bdde4bfa2c7
Source dataset
uspto-grants-1998_09
Patent number
US05808124

Reaction notes

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