Water → HCID 66618711, compound

HRID 406337Notes

Reaction equation

HRID 406337 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[F:48][C:49]([F:60])([F:59])[C:50]1[CH:51]=[C:52](B(O)O)[CH:53]=[CH:54][CH:55]=1.[O:61]1[CH2:66][CH2:65][CH:64]=[CH:63][C:62]1=[O:67]>O1CCOCC1>[F:48][C:49]([F:60])([F:59])[C:50]1[CH:51]=[C:52]([CH:64]2[CH2:65][CH2:66][O:61][C:62](=[O:67])[CH2:63]2)[CH:53]=[CH:54][CH:55]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5206603393-45-1HCID 634876Binap, (A+-)-HCID 27343883-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 66618711HCID 66618711, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(Acetylacetonato)bis(ethylene)rhodium (I) (180 mg) was dissolved in 1,4-dioxane (144 mL). Racemic BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthalene) (867 mg) was added at room temperature, followed by stirring for 30 minutes. Subsequently, water (14.4 mL) and 3-(trifluoromethyl)phenylboronic acid (5.29 g) were added, followed by stirring for 10 minutes. Then, 5,6-dihydro-2H-pyran-2-one (2 mL) was added and the mixture was reacted at 100° C. for 12 hours. The reaction solution was partitioned with ethyl acetate and water. Then, the organic layer was washed with a saturated sodium bicarbonate solution and dried over magnesium sulfate. Concentration under reduced pressure gave an oil. The oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 60%) to obtain the title compound (2.5 g).

Workup

  1. stirringby stirring for 10 minutes
  2. customthe mixture was reacted at 100° C. for 12 hours
  3. customThe reaction solution was partitioned with ethyl acetate and water
  4. washThen, the organic layer was washed with a saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationConcentration under reduced pressure
  7. customgave an oil
  8. customThe oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 60%)

Sources & evidence

ORD record
ord-58efa0646ff245c384993606426da58e
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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