Methanol → HCID 77231251, compound

HRID 1187084Notes

Reaction equation

HRID 1187084 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7](O)=[C:8]([CH:11]=1)[CH:9]=[O:10])[CH:2]=[CH2:3].C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.CCN(CC)CC.CN([CH:46]=[O:47])C.[CH3:48][OH:49]>ClCCl.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]>[CH2:1]([C:4]1[CH:5]=[C:6]([O:13][CH3:14])[C:7]([C:48]([O:47][CH3:46])=[O:49])=[C:8]([CH:9]=[O:10])[CH:11]=1)[CH:2]=[CH2:3]

Participants

8

Reactant 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 142176Phenyl triflimideHCID 17138875-allyl-2-hydroxy-3-methoxybenzaldehyde

Product 1

HCID 77231251HCID 77231251, compound

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a flask containing 5-allyl-2-hydroxy-3-methoxybenzaldehyde (5.0 g, 26.0 mmol) and N-phenyl-trifluoromethanesulfonimide was added DCM (75 mL). The flask was placed at 0° C. and treated with Et3N (4 mL) and stirred for 2 days at room temp. The mixture was diluted with dichloromethane and washed with 1N HCl, saturated sodium bicarbonate solution, and brine, then dried (Na2SO4) and concentrated. The residue in a flask was treated with dppf (0.18 g, 0.45 mmol), PdOAc2 (0.1 g, 0.44 mmol), and Et3N (8 mL, 56 mmol) followed by addition of DMF (45 mL) and MeOH (30 mL). The reaction mixture was then degassed and purged with CO 3 times and stirred under CO for 6 h at 70° C. When LC indicated consumption of starting material, the solution was concentrated to dryness. The organic residue was purified by MPLC (hexanes/EtOAc=1/0.2) to provide methyl 4-allyl-2-formyl-6-methoxybenzoate.

Workup

  1. customwas placed at 0° C.
  2. washwashed with 1N HCl, saturated sodium bicarbonate solution, and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe reaction mixture was then degassed
  6. custompurged with CO 3 times
  7. stirringstirred under CO for 6 h at 70° C
  8. customconsumption of starting material
  9. concentrationthe solution was concentrated to dryness
  10. customThe organic residue was purified by MPLC (hexanes/EtOAc=1/0.2)

Sources & evidence

ORD record
ord-459d7c29f3eb431e9b4a710ade36cf60
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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