Potassium Carbonate → HCID 59187023, compound

HRID 1686090Notes

Reaction equation

HRID 1686090 reaction equation
C([O:4][C:5]1[C:10]([O:11][CH2:12][CH:13]=[CH2:14])=[C:9]([O:15][CH3:16])[CH:8]=[CH:7][C:6]=1[C:17](=[O:27])[CH2:18][C:19]1[C:24]([Cl:25])=[CH:23][N:22]=[CH:21][C:20]=1[Cl:26])C=C.C([O-])([O-])=O.[K+].[K+]>CO.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>[CH2:12]([O:11][C:10]1[C:5]([OH:4])=[C:6]([C:17](=[O:27])[CH2:18][C:19]2[C:24]([Cl:25])=[CH:23][N:22]=[CH:21][C:20]=2[Cl:26])[CH:7]=[CH:8][C:9]=1[O:15][CH3:16])[CH:13]=[CH2:14]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 24959215HCID 24959215, compound

Product 1

HCID 59187023HCID 59187023, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(2,3-Bis-allyloxy-4-methoxy-phenyl)-2-(3,5-dichloro-pyridin-4-yl)-ethanone from example 6 (3.9 g, 9.55 mmol) was dissolved in MeOH (96 mL) and cooled to 0° C. under argon. Pd(PPh3)4 (100 mg, 0.0955 mmol) was added followed by K2CO3 (1.3 g, 9.55 mmol). The cooling bath was removed and the reaction mixtured was stirred for 3 hours and then evaporated in vacuo. The crude was redissolved in EtOAc (100 mL) and washed twice with NH4Cl (sat, 50 mL). The organic phase was dried over Na2SO4 and evaporated in vacuo and purified by flash chromatography using a gradient of toluene and 2% EtOAc as eluent. 1-(3-Allyloxy-2-hydroxy-4-methoxy-phenyl)-2-(3,5-dichloro-pyridin-4-yl)-ethanone was obtained as a white solid. 1H NMR (CDCl3) δ=11.90 (1H, s), 8.53 (2H, s), 7.68 (1H, d), 6.58 (1H, d), 6.10 (1H, m), 5.26 (2H, m), 4.66 (2H, s), 4.59 (2H, d), 3.96 (3H, s). Yield 2.2 g (64%)

Workup

  1. customThe cooling bath was removed
  2. customthe reaction
  3. customevaporated in vacuo
  4. dissolutionThe crude was redissolved in EtOAc (100 mL)
  5. washwashed twice with NH4Cl (sat, 50 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated in vacuo
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8294327a108e470fb87ea86e01ccc791
Source dataset
uspto-grants-2012_04
Patent number
US08148537B2

Reaction notes

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