Water → HCID 11850964, compound

HRID 2246672Notes

Reaction equation

HRID 2246672 reaction equation
C[B-](F)(F)F.[K+].[CH2:7](Cl)Cl.FC(F)(F)S(O[C:16]1[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[CH:19]=[C:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:17]=1)(=O)=O.O>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:7][C:16]1[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[CH:19]=[C:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 23692566Potassium Trifluoro(methyl)borateHCID 59218523HCID 59218523, compound

Product 1

HCID 11850964HCID 11850964, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

The ester is formed according to the method of Molander et al. (J. Org. Chem. 68, 5534, (2003)). To a stirring suspension of potassium methyltrifluoroborate (629.0 mg, 5.2 mmol) Cs2CO3 (5.0 g, 15.5 mmol), PdCl2(dppf).CH2Cl2 (46.0 mg, 0.057 mmol), and triflate (46.3) (2.0 g, 5.7 mmol) in 50 mL THF is added water (5 mL) under an argon atmosphere. Stirring the mixture at reflux until TLC confirms the consumption of the starting material. The mixture is cooled to room temperature, and is diluted with water and extracted with ether. The combined organic layers are dried (MgSO4) and concentrated under reduced pressure. The residue is purified by column chromatography (silica, EtOAc/Hexane), to afford ester 46.4.

Workup

  1. temperatureat reflux until TLC
  2. customthe consumption of the starting material
  3. additionis diluted with water
  4. extractionextracted with ether
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography (silica, EtOAc/Hexane)

Sources & evidence

ORD record
ord-238fd8ff245c44fbbf13510e519f22cb
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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