Methanol → HCID 57890029, compound

HRID 1819958Notes

Reaction equation

HRID 1819958 reaction equation
[CH2:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15](OS(C(F)(F)F)(=O)=O)=[C:14](C)[CH:13]=1)([C:6]1[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:4][CH3:5])[CH3:2].C(N([CH2:32][CH3:33])CC)C.[CH3:34][OH:35].[C]=[O:37]>CC([O-])=O.CC([O-])=O.[Pd+2].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.[Fe+2].CN(C)C=O>[CH3:34][O:35][C:14](=[O:37])[C:15]1[CH:16]=[CH:17][C:12]([C:3]([CH2:4][CH3:5])([C:6]2[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=2)[CH2:1][CH3:2])=[CH:13][C:32]=1[CH3:33]

Participants

8

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 57890182HCID 57890182, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 57890029HCID 57890029, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-methyl-thiophen-2-yl) propyl]-2-methyl-phenyl ester (12 g, 29.62 mmol), Pd(OAc)2 (699 mg, 3 mmol), dppf (3.3 g, 6 mmol), triethylamine (12.5 ml, 90 mmol), methanol (12 ml, 300 mmol), and N,N-dimethylformamide (40 ml) is treated with carbon monoxide (1000 psi) at 110° C. in a Parr-reactor for 48 h. The reaction is concentrated, dissolved in is evaporated in EtOAc and filtered through a silica gel pad. The filtrate is concentrated and chromatographed (Hex to 10% EtOAc/Hex) to give the title compound (6.9 g, 73%).

Workup

  1. concentrationThe reaction is concentrated
  2. dissolutiondissolved
  3. customin is evaporated in EtOAc
  4. filtrationfiltered through a silica gel pad
  5. concentrationThe filtrate is concentrated
  6. customchromatographed (Hex to 10% EtOAc/Hex)

Sources & evidence

ORD record
ord-c4e628414a554c71991907f7629ce4ef
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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