Perchloric Acid → HCID 67126266, compound

HRID 514040Notes

Reaction equation

HRID 514040 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([C:7]1[C:16]([CH3:17])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:18][CH3:19])[C:8]=1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[OH:6])[CH3:2].Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(OC(C)(C)C)(=O)C>[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:6][C:7]([CH3:16])([CH3:8])[CH3:5])[C:7]1[C:16]([CH3:17])=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:18][CH3:19])[C:8]=1[C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24247Perchloric Acid2×HCID 516892Sodium BicarbonateHCID 67126136HCID 67126136, compound

Product 1

HCID 67126266HCID 67126266, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

A solution of [1-(4-chloro-phenyl)-5-methoxy-3-methyl-naphthalen-2-yl]-hydroxy-acetic acid ethyl ester (23 mg) and perchloric acid, 70% (3 μL) in tert-butyl acetate (1 mL) was stirred at room temperature for 2 h. After 2 h, the reaction had apparently stalled, so 3 μL additional perchloric acid was added. After 2 additional hours, no further conversion was observed (LCMS analysis). Saturated sodium bicarbonate solution was added and the mixture was extracted with ethyl acetate (3×). The combined organic layer was dried (Na2SO4), and concentrated. The crude mixture was purified by flash column chromatography to give tert-butoxy-[1-(4-chloro-phenyl)-5-methoxy-3-methyl-naphthalen-2-yl]-acetic acid ethyl ester (9 mg) plus 7 mg of recovered starting material. The recovered starting material was re-subjected to similar reaction conditions to yield an additional 3 mg of desired. 1H-NMR: 400 MHz, (CDCl3) δ: 8.10 (s, 1H), 7.39-7.48 (m, 3H), 7.25 (s, 1H), 7.17 (app t, 1H), 6.78 (app t, 2H), 5.09 (s, 1H), 4.06-4.20 (m, 2H), 3.99 (s, 3H), 2.61 (s, 3H), 1.185 (t, 3H), 0.98 (s, 9H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. dry with materialThe combined organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude mixture was purified by flash column chromatography

Sources & evidence

ORD record
ord-665a855c58dc4f3aa1727e7a3682c99f
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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