Water → HCID 59218387, compound

HRID 2246685Notes

Reaction equation

HRID 2246685 reaction equation
I/[CH:2]=[CH:3]/[C@@H:4]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[CH:13][CH:12]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[Br-].[CH2:25]([Zn+])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.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>[C:26]1([CH2:25]/[CH:2]=[CH:3]/[C@H:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][O:19]3)=[CH:13][CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 962WaterHCID 57801813HCID 57801813, compoundHCID 178419772HCID 178419772, compound

Product 1

HCID 59218387HCID 59218387, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 83.4 (571.9 mg, 1.33 mmol, 1 eq., MW 430.29) in THF (15 mL) at 23° C. was added Pd(PPh3)4 (153.6 mg, 0.133 mmol, 0.1 eq., MW 1155.58) followed by dropwise addition of benzylzinc bromide solution (3.2 mL, 1.6 mmol, 1.2 eq., 0.5 M). After 17.5 hours, water (10 mL) was added to quench the reaction. The mixture was extracted with EtOAc (2×50 mL), dried with MgSO4, and filtered. The organic layer was concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated providing a colorless oil that was used without further purification.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with EtOAc (2×50 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationThe organic layer was concentrated in vacuo
  7. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0 to 20% EtOAc in hexanes)
  8. additionFractions containing the desired product
  9. concentrationconcentrated
  10. customproviding a colorless oil that
  11. customwas used without further purification

Sources & evidence

ORD record
ord-d24682de09284ac6894ec424d61cb0a6
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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