Methanol → HCID 18536036, compound

HRID 412189Notes

Reaction equation

HRID 412189 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10]C(I)=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:7]2.C(N([CH2:23][CH3:24])CC)C.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[OH2:54].[CH3:55][OH:56]>CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:1][C:2]1[C:3]2[C:8](=[CH:7][C:6]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:5][CH:4]=2)[C:23]([C:24]([O:56][CH3:55])=[O:54])=[CH:10][CH:11]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 18536114HCID 18536114, compound

Product 1

HCID 18536036HCID 18536036, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the the product from Step E (954 mg, 2.23 mmol) in 7 mL of methanol and 7 mL of DMSO was added triethylamine (1.56 mL, 11.2 mmol), Pd(OAc)2 (25.1 mg, 0.11 mmol), and 1,3-bis-(diphenylphosphine)propane (46 mg, 0.11 mmol). The reaction was heated at 50° C. under an atmosphere of carbon monoxide for 3 hours, and cooled to room temperature. The solution was poured into water and extracted with 3× dichloromethane. The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the product which was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with 3× dichloromethane
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the product which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-f1d33486d1024ac48cf3a560dd59ff01
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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