Perchloric Acid → HCID 67126075, compound

HRID 514050Notes

Reaction equation

HRID 514050 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[CH:11]=[C:10]([CH3:20])[C:9]=2[CH:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=O>C(OC(=O)C)(C)(C)C>[C:5]([O:27][CH:21]([C:9]1[C:10]([CH3:20])=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23])([CH3:8])([CH3:6])[CH3:4]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 67126122HCID 67126122, compound

Product 1

HCID 67126075HCID 67126075, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a solution of ethyl 2-(1-(4-chlorophenyl)-6-methoxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate (27 mg, 0.07 mmol) in tert-butylacetate (1.0 mL) was added 70% perchloric acid (0.012 mL, 0.14 mmol) and the reaction was stirred at room temperature for 1.5 hours. The reaction was quenched with solid sodium bicarbonate, water (2 mL) added and stirred 1 hour. The product was extracted with ethyl acetate, concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a colorless oil (16.2 mg). 1H-NMR: 400 MHz, (CDCl3) δ: 7.48 (s, 1H), 7.41-7.36 (m, 3H), 7.19 (d, J=6.4 Hz, 1H), 7.06 (d, J=9.2 Hz, 1H), 6.99 (br s, 1H), 6.86 (d, J=9.2 Hz, 1H), 5.00 (s, 1H), 4.12-4.02 (m, 2H), 3.82 (s, 3H), 2.52 (s, 3H), 1.13 (t, J=7.2 Hz, 3H), 0.91 (s, 9H).

Workup

  1. customThe reaction was quenched with solid sodium bicarbonate, water (2 mL)
  2. additionadded
  3. stirringstirred 1 hour
  4. extractionThe product was extracted with ethyl acetate
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ebdae97b83c04167b795ae030797ca2c
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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