Ethyl 2-methylacetoacetate → 5-Ethyloxycarbonyl-5-methyl-6-oxo-1-heptanesulfonic acid

HRID 516428

Reaction equation

HRID 516428 reaction equation
[CH2:1]1[CH2:8][O:7][S:4](=[O:6])(=[O:5])[CH2:3][CH2:2]1.[CH3:9][CH:10]([C:16]([CH3:18])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(O[K])(C)(C)C>C(O)(C)(C)C>[CH2:14]([O:13][C:11]([C:10]([CH3:9])([C:16](=[O:17])[CH3:18])[CH2:8][CH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5])=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 154111,4-Butane sultoneHCID 178418922HCID 178418922, compound

Product 1

HCID 580840065-Ethyloxycarbonyl-5-methyl-6-oxo-1-heptanesulfonic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

0.35 ml (3.47 mmol) of 1,4-butane sultone were added to a mixture of 0.49 ml (3.47 mmol) ethyl 2-methylacetoacetate and 513 mg (4.2 mmol) of tert-BuOK in 12 ml tert-butanol and refluxed for 15 hours. The formed precipitate was filtered and washed with hexane to yield 730 mg of 5-ethyloxycarbonyl-5-methyl-6-oxo-1-heptanesulfonic acid. δH (200 MHz, DMSO-d6): 4.12 (2H, q, 7.1, 14.2 Hz, OCH2), 3.97 (2H, t, 5.8 Hz, CH2SO3H), 2.10 (3H, s, COCH3), 1.78-1.41 (4H, m, CH2), 1.24-1.01 (2H, m, CH2), 1.22 (3H, s, CCH3), 1.17 (3H, t, 7.3 Hz, CH2CH3).

Workup

  1. temperaturerefluxed for 15 hours
  2. filtrationThe formed precipitate was filtered
  3. washwashed with hexane

Sources & evidence

ORD record
ord-2e1a968278cf48e39fc4abe11e9aaf6f
Source dataset
uspto-grants-2015_08
Patent number
US09110069B2

Linked notes

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