1,2-Dichloroethane → HCID 44139977, compound

HRID 2110582Notes

Reaction equation

HRID 2110582 reaction equation
[CH2:1]([C:4]1([NH:16][O:17][CH3:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[CH:6]=[C:5]1O)[CH:2]=C.[CH:19](=[O:23])[CH:20]([CH3:22])[CH3:21].[C:24](O)(=O)C.S([O-])([O-])(=O)=O.[Mg+2].Cl[CH2:35][CH2:36]Cl>>[CH:20]([CH:19]1[N:16]([O:17][CH3:18])[C:4]2([CH2:1][CH:2]=[C:35]([CH3:36])[CH3:24])[C:13]3[C:8]([C:7](=[O:14])[CH:6]=[C:5]2[O:23]1)=[CH:9][CH:10]=[CH:11][CH:12]=3)([CH3:22])[CH3:21]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 6561IsobutyraldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 178440464HCID 178440464, compound

Product 1

HCID 44139977HCID 44139977, compoundYield 73%

Procedure

To a solution of Example 7B (800 mg, 3.3 mmol) in 1,2-dichloroethane (25 mL) was added isobutyraldehyde (1.8 mL, 19.6 mmol), acetic acid (0.37 mL, 6.5 mmol) and magnesium sulfate (2.5 g). The solution was stirred at room temperature overnight, filtered, and the filtrate washed with 10% NaHCO3 (2×20 mL) and brine (1×20 mL) and the resulting solution dried (MgSO4), the drying agent filtered off and the solvent removed in vacuo to give a crude residue which was purified by column chromatography on silica gel (20% ethyl acetate/hexane) to give the title compound as a colorless solid (710 mg, 73%). 1H NMR (d6-DMSO) δ 7.94, 7.91 (d, 1H), 7.75-7.63 (m, 2H), 7.51-7.43 (m, 1H), 5.62, 5.56 (d, 1H), 5.17-5.04 (m, 1H), 4.89, 4.85 (d, 1H), 4.80, 4.74 (d, 1H), 3.48 (s, 3H), 2.76-2.66 (m, 1H), 2.64-2.53 (m, 1H), 2.44-2.30 (m, 1H), 1.22-1.08 (m, 6H); MS (ESI) m/z 300 (M+H+).

Workup

  1. filtrationfiltered
  2. washthe filtrate washed with 10% NaHCO3 (2×20 mL) and brine (1×20 mL)
  3. dry with materialthe resulting solution dried (MgSO4)
  4. filtrationthe drying agent filtered off
  5. customthe solvent removed in vacuo
  6. customto give a crude residue which
  7. customwas purified by column chromatography on silica gel (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1b2f79a28b3f4a80853dcd171ac91506
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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