Tetrahydrofuran → HCID 18316645, compound

HRID 275806Notes

Reaction equation

HRID 275806 reaction equation
Br[C:2]1[C:10]2[O:9][CH:8]=[N:7][C:6]=2[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:40].[O:41]1[CH2:45]CCC1>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>[CH3:12][O:11][C:5]1[C:6]2[N:7]=[CH:8][O:9][C:10]=2[C:2]([C:45]([OH:41])=[O:40])=[CH:3][CH:4]=1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 18316640HCID 18316640, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 18316645HCID 18316645, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

7-Bromo-4-methoxybenzoxazole (630 mg), triethylamine (3.85 ml), triphenylphosphine (290 mg), bis(triphenylphosphine)palladium chloride (88 mg), water (20 ml) and tetrahydrofuran (40 ml) were combined and heated to 90° C. in a Parr apparatus under 1035 kPa (150 psi) of carbon monoxide for 3 days. After cooling to room temperature, the tetrahydrofuran was evaporated. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The aqueous phase was acidified to pH4 with acetic acid, and the layers separated. The aqueous phase was extracted with ethyl acetate (2×30 ml) followed by dichloromethane (2×30 ml). The combined organic phases were dried over magnesium sulphate and evaporated in vacuo. Purification of the residue by flash chromatography eluting with ethyl acetate and trituration with diethyl ether afforded the title compound as a white solid (125 mg). On standing, a white solid precipitated in the water layer which was removed by filtration and dried in vacuo at 45° C. for 1 hour to give a further portion of the title compound as a white solid (49 mg).

Workup

  1. customthe tetrahydrofuran was evaporated
  2. customThe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×30 ml)
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. customevaporated in vacuo
  7. customPurification of the residue by flash chromatography
  8. washeluting with ethyl acetate and trituration with diethyl ether

Sources & evidence

ORD record
ord-ae1435cb3fc045feadbc8ae0aa578b4f
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Reaction notes

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