Sodium Carbonate → HCID 70818081, compound

HRID 591051Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2-[5-(3,4-dihydro-2H-1-benzopyran-6-yl)-1,3-dimethyl-1H-pyrazol-4-yl]-2-hydroxyacetate (27c) (72 mg, 0.227 mmol) in tert-butyl acetate (6 mL) at 0° C. was added perchloric acid (0.75 mL). The mixture was stirred at 0° C. for 3 hours at room temperature before being poured into a saturated aqueous solution of sodium carbonate (30 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 mL). The organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 50/50) to provide the desired product (27d) (51 mg, 0.137 mmol, 60%) as a colorless oil.

Workup

customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
dry with materialThe organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 50/50)

Sources & evidence

ORD record: ord-7f705039d4d0494e937198c9f5bd87d9
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238026B2

Reaction notes

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