Water → Sulfate(1-), (3-carboxylato-5-methylphenyl)pentafluoro-, hydrogen (1:1), (OC-6-21)-

HRID 1055654Notes

Reaction equation

HRID 1055654 reaction equation
C[Al](C)C.[CH3:5]CCCCC.Br[C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([S:21]([F:26])([F:25])([F:24])([F:23])[F:22])[CH:20]=1)[C:15]([OH:17])=[O:16].O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:5][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([S:21]([F:26])([F:25])([F:24])([F:23])[F:22])[CH:20]=1)[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 16682925TrimethylaluminumHCID 58137421HCID 58137421, compound

Product 1

HCID 66523589Sulfate(1-), (3-carboxylato-5-methylphenyl)pentafluoro-, hydrogen (1:1), (OC-6-21)-

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

1.15 ml (2.29 mmol) of a 2 M solution of trimethylaluminium in a hexane fraction were added to a solution of 250 mg (0.764 mmol) of the compound of Example 15A and 27 mg (0.023 mmol) of tetrakis(triphenylphosphine)palladium(0) in 2.5 ml of anhydrous THF, and the mixture was then, under an argon atmosphere, heated in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 150° C. for 120 min. After cooling to RT, about 10 ml of water were added, and the reaction mixture was extracted three times with in each case about 10 ml of ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and then concentrated to dryness on a rotary evaporator. The product was isolated by preparative HPLC (Method 9). Concentration of the product fractions and drying of the residue under high vacuum gave 98 mg (47% of theory, 95% pure) of the title compound.

Workup

  1. temperatureAfter cooling to RT
  2. extractionthe reaction mixture was extracted three times with in each case about 10 ml of ethyl acetate
  3. washThe combined organic extracts were washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness on a rotary evaporator
  7. customThe product was isolated by preparative HPLC (Method 9)
  8. customConcentration of the product fractions and drying of the residue under high vacuum

Sources & evidence

ORD record
ord-eb5b2df0583b4b52bcb99c30d943be22
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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