Acetonitrile → HCID 68871458, compound

HRID 494634Notes

Reaction equation

HRID 494634 reaction equation
C([C:3](CC)([C:7]([O-:9])=[O:8])[C:4]([O-:6])=[O:5])C.[Cl-].[Mg+2].[Cl-].[CH2:15](N(CC)CC)[CH3:16].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([CH3:39])([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[C:31](Cl)=[O:32])=[CH:26][CH:25]=1.[C:40](#N)[CH3:41]>>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([CH3:39])([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[C:31]([CH:3]([C:7]([O:9][CH2:40][CH3:41])=[O:8])[C:4]([O:6][CH2:15][CH3:16])=[O:5])=[O:32])=[CH:26][CH:25]=1

Participants

6

Reactant 5

HCID 6342Acetonitrile2×HCID 8471TriethylamineHCID 5360315Magnesium ChlorideHCID 69515632,2-DiethylpropanedioateHCID 876088622-(4-Methoxyphenyl)-2,5-dimethylhexanoyl chloride

Product 1

HCID 68871458HCID 68871458, compound

Conditions

Temperature
0 °C

Procedure

To a solution of diethylmalonate (5.45 g, 0.034 mol) in 80 mL acetonitrile at 0° C. was added magnesium chloride (3.24 g, 0.034 mol) and triethylamine (10 mL, 0.066 mol). The slurry was stirred at 0° C. for fifteen minutes and then room temperature for two hours. The slurry was then cooled to 0° C. where a solution of Example 155D (0.034 mol) in 100 mL acetonitrile was added. The slurry was heated at 50° C. for 18 hours. The solvent was removed under vacuum and residue portioned between ethyl acetate and 1 N HCl. The organic layer was dried with anhydrous magnesium sulfate and concentrated to yield 14.0 grams of product. A sample was purified on silica using 25% ethyl acetate in hexane. 1H NMR (300 MHz, CDCl3): δ ppm 0.83 (d, J=6.25 Hz, 3H) 0.86 (d, J=6.62 Hz, 3H) 1.06 (m, 2H) 1.19 (ddd, J=12.69, 7.17, 6.99 Hz, 6H) 1.49 (s, 3H) 1.93 (dd, J=9.01, 7.91 Hz, 2H) 3.80 (s, 3H) 4.06 (m, 2H) 4.11 (q, J=7.11 Hz, 2H) 4.53 (s, 1H) 6.87 (m, 2H) 7.18 (m, 2H).

Workup

  1. additionwas added
  2. temperatureThe slurry was heated at 50° C. for 18 hours
  3. customThe solvent was removed under vacuum and residue
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ca5e2c7d8ac24ca28ac538952c72c1a7
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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