Hydrochloric Acid → HCID 86087051, compound

HRID 1992990Notes

Reaction equation

HRID 1992990 reaction equation
[CH3:1][C:2]1[C:3](=[O:18])[C:4]([O:16]C)(OC)[C:5]=1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([Mg]Br)[CH:24]=[CH:25][CH:26]=1.Cl>C1COCC1>[OH:18][C:3]1([C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([O:20][CH3:19])[CH:26]=2)[C:4](=[O:16])[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)=[C:2]1[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86087049HCID 86087049, compoundHCID 178490745HCID 178490745, compound

Product 1

HCID 86087051HCID 86087051, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF solution (12 mL) of 2-methyl-4,4-bis(methyloxy)-3-[3-(methyloxy)phenyl]-2-cyclobuten-1-one (245) (0.500 g, 2.02 mmol, 1 equiv) was cooled to ca. −78° C. 3-Methoxyphenylmagnesium bromide (3.02 mL, 1.0 M, 1.5 equiv) was added. After 5 min, aqueous HCl (3 N, 20 mL) was added. Extraction with EtOAc (3×20 mL) was followed by washing with 50% aqueous NaHCO3, drying (Na2SO4), filtration, and concentration to a bright yellow oil. Radial chromatography (SiO2, 4 mm plate, 80:20; hexanes/EtOAc) afforded the title compound (246) as a bright yellow oil (0.515 g, 82%). 1H NMR (CDCl3, 300 MHz) δ 7.39-7.29 (m, 4H), 7.10-6.88 (m, 4H), 3.88 (s, 3H), 3.85 (s, 3H), 2.47 (s, 3H); TLC (60:40; hexanes/EtOAc): Rf=0.23.

Workup

  1. extractionExtraction with EtOAc (3×20 mL)
  2. washby washing with 50% aqueous NaHCO3
  3. customdrying
  4. filtration(Na2SO4), filtration, and concentration to a bright yellow oil

Sources & evidence

ORD record
ord-1387b4483ccf493693c0031bca782498
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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