Hydrochloric Acid → HCID 68536766, compound

HRID 1992862Notes

Reaction equation

HRID 1992862 reaction equation
[CH3:1][CH:2]([CH3:17])[CH:3]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[CH2:4][C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl.CN(C=O)C>[CH3:17][CH:2]([CH:3]1[CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[C:5](=[O:7])[CH2:4]1)[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 68534647HCID 68534647, compound

Product 1

HCID 68536766HCID 68536766, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-3-{[3-(methyloxy)phenyl]methyl}pentanoic acid (67) (0.15 g, 0.63 mmol) in CH2Cl2 (5 mL) was added oxalyl chloride (0.17 mL, 1.90 mmol) followed by one drop of DMF. The mixture was stirred at room temperature overnight. CH2Cl2 and excess of oxalyl chloride were removed under vacuum. The residue was dissolved in CH2Cl2 (10 mL), cooled in an ice bath, AlCl3 (0.13 g, 0.95 mmol) was added. The resulting mixture was stirred at 0° C. for 4 h. Poured into 1 N HCl (7 mL) with ice, and the mixture was extracted with CH2Cl2. The extracts were combined and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a brown oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (8:1) to give 0.112 g (81%) of the title compound (68) as a light yellow viscous oil, which solidified after standing. 1H NMR (400 MHz, CDCl3): δ 0.97 (d, J=6.8 Hz, 3H), 0.98 (d, J=6.7 Hz, 3H), 1.60-1.70 (m, 1H), 1.90-2.05 (m, 1H), 2.30 (dd, J1=16.5 Hz, J2=2.8 Hz, 1H), 2.65-2.80 (m, 1H), 2.85-2.95 (m, 1H), 3.85 (s, 3H), 6.71 (d, J=2.2 Hz, 1H), 6.81 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.98 (d, J=8.8 Hz, 1H).

Workup

  1. customCH2Cl2 and excess of oxalyl chloride were removed under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2 (10 mL)
  3. temperaturecooled in an ice bath
  4. stirringThe resulting mixture was stirred at 0° C. for 4 h
  5. extractionthe mixture was extracted with CH2Cl2
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customto give the crude product as a brown oil
  11. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (8:1)

Sources & evidence

ORD record
ord-6712bc9de143468fac57872ea9479d01
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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