Formic Acid → HCID 23114026, compound

HRID 2376373Notes

Reaction equation

HRID 2376373 reaction equation
FC(F)(F)S(O[C:7]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]2[O:11][CH2:12][CH:13]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=3)[C:9]=2[C:8]=1[CH3:29])(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CCCC)CCCC)CCC.C(O)=O>C1(C)C=CC=CC=1.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>[CH:20]([C:17]1[CH:18]=[CH:19][C:14]([CH:13]2[CH2:12][O:11][C:10]3[C:23]4[C:28]([CH:7]=[C:8]([CH3:29])[C:9]2=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:15][CH:16]=1)([CH3:22])[CH3:21]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 7622TributylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 23113879HCID 23113879, compound

Product 1

HCID 23114026HCID 23114026, compoundYield 18%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-(4-isopropylphenyl)-4-methyl-2,3-dihydronaphtho[1,2-b]furan-5-yl trifluoromethanesulfonate obtained in Reference Example 253 (2.23 g, 4.96 mmol), dichlorobis(triphenylphosphine)palladium (210 mg, 0.30 mmol), 1,3-bis(diphenylphosphino)propane (310 mg, 0.750 mmol) and tributylamine (5 mL, 21 mmol) in toluene (15 mL) was added formic acid (0.5 mL) at room temperature, and the mixture was stirred under argon atmosphere at 90° C. for 16 hours. Water was added to the reaction solution, which was extracted with ethyl acetate, the organic layer was washed with water and a saturated brine and then was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20) to obtain 270 mg (yield 18%) of the title compound. Oily matter.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materiala saturated brine and then was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-33809885d82c4fda885ddddac8428f81
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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