Hydrochloric Acid → HCID 90423706, compound

HRID 531005Notes

Reaction equation

HRID 531005 reaction equation
C1(P(C2CCCCC2)[C:8]2C=CC=C[C:9]=2[C:14]2C(OC)=CC=CC=2OC)CCCCC1.[CH2:30]([O:32][C:33]1[CH:34]=[C:35]([CH:38]=[C:39](I)[C:40]=1[O:41]COC)[CH:36]=[O:37])[CH3:31].C1(B(O)O)CC1.C(=O)([O-])[O-].[Na+].[Na+].Cl>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO.O.C1(C)C=CC=CC=1>[CH:14]1([C:39]2[CH:38]=[C:35]([CH:34]=[C:33]([O:32][CH2:30][CH3:31])[C:40]=2[OH:41])[CH:36]=[O:37])[CH2:9][CH2:8]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 90422892HCID 90422892, compound

Product 1

HCID 90423706HCID 90423706, compoundYield 594.5%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

Tris(dibenzylideneacetone)dipalladium(0) (2.30 g) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (2.21 g) were added to a mixture of 3-ethoxy-5-iodo-4-(methoxymethoxy)benzaldehyde (12.1 g), cyclopropylboronic acid (9.25 g), a 2 M aqueous sodium carbonate solution (53.9 mL), and toluene (60 mL), and the resultant mixture was stirred at 100° C. for 2 hours in an argon atmosphere. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain a purified product. 6 M hydrochloric acid (50 mL) was added to a methanol (100 mL) solution of the obtained purified product, and the mixture was stirred at 70° C. for 3 hours, and then, the solvent was distilled off under reduced pressure, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (6.60 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  5. customto obtain a purified product
  6. custompurified product
  7. distillationthe solvent was distilled off under reduced pressure
  8. extractionfollowed by extraction with ethyl acetate
  9. washThe obtained organic layer was washed with water and saturated saline
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6bccc5429adf4da0b0415cc81676cf81
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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