Ethyl Acetate → HCID 15622822, compound

HRID 327217Notes

Reaction equation

HRID 327217 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:18]2[C:19](=[O:28])[C:20]([CH3:27])=[C:21]([CH3:26])[C:22](=[O:25])[C:23]=2[CH3:24])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16])=[CH:5][CH:4]=1.Cl.[NH2:30][OH:31].C(=O)([O-])O.[Na+].C(OCC)(=O)C>ClCCl.C(Cl)(=O)C(Cl)=O.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:18]2[C:19](=[O:28])[C:20]([CH3:27])=[C:21]([CH3:26])[C:22](=[O:25])[C:23]=2[CH3:24])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:30][OH:31])=[O:16])=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 15622821HCID 15622821, compound

Product 1

HCID 15622822HCID 15622822, compoundYield 45.5%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 65578Oxalyl chlorideSolvent

Conditions

Temperature
50 °C

Procedure

7-(4-Methoxyphenyl)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-heptanoic acid (1.3 g, 3.3 mmol) was dissolved in dichloromethane (20 ml), to which oxalyl chloride (1 ml) was added at room temperature. The reaction mixture was stirred at 50° C. for 1 hour, and the solvent was evaporated under reduced pressure. The resultant residue was dissolved in THF (5 ml), which was added dropwise at room temperature to a mixture of hydroxylamine hydrochloride (1 g, 14 mmol) in THF (10 ml) and saturated solution of aqueous sodium hydrogencarbonate (10 ml). After being stirred at room temperature for 1 hour, ethyl acetate (20 ml) was added to the reaction mixture. The organic layer was washed with water, dried, and concentrated under reduced pressure, to give 7-(4-methoxyphenyl)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-heptanohydroxamic acid (0.6 g, 42%). The physical properties are shown in the column of Compound No.8 in Table 1. In the similar manner, Compounds Nos. 1, 4, 10, 11, 12, 13, 14, 15, 16, 17, 19, 20, 21, 22, 23, 24, 25, and 26 were synthesized.

Workup

  1. additionwas added at room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe resultant residue was dissolved in THF (5 ml)
  4. stirringAfter being stirred at room temperature for 1 hour
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfba81da5f614e1daf7cda45e79af44d
Source dataset
uspto-grants-1993_12
Patent number
US05272180

Reaction notes

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