Acetaldehyde → Ethyl 4-methyl-5-(6-methyl-3,6-dihydro-2H-pyran-2-yl)isoxazole-3-carboxylate

HRID 1478191Notes

Reaction equation

[OH:1][CH:2]([C:6]1[O:10][N:9]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:7]=1[CH3:16])[CH2:3][CH:4]=[CH2:5].[CH:17](=O)[CH3:18].[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[Cl-].[NH4+]>C(Cl)Cl>[CH3:16][C:7]1[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:9][O:10][C:6]=1[CH:2]1[CH2:3][CH:4]=[CH:5][CH:17]([CH3:18])[O:1]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 5-(1-hydroxybut-3-en-1-yl)-4-methylisoxazole-3-carboxylate (35 mg, 0.155 mmol) in DCM (1 mL) was treated with acetaldehyde (8.72 μl, 0.155 mmol) and the reaction mixture was cooled to 0° C. A solution of TMSOTf (80.4 μL, 0.465 mmol) in DCM (1.5 mL) cooled to 0° C. was added and the reaction mixture was stirred at 0° C. for 30 minutes and at room temperature overnight. To the resulting mixture was added a saturated solution of ammonium chloride (aq) (2 mL) and this was extracted with DCM (×3). The combined organic extracts were passed through a phase separating cartridge and the eluent was concentrated under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 0-100% EtOAc in iso-hexane afforded the title compound;

Workup

additionwas added
extractionthis was extracted with DCM (×3)
customseparating cartridge
concentrationthe eluent was concentrated under reduced pressure
customThe crude material was adsorbed onto silica and purification by chromatography
washeluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record: ord-340c3bd3c0644439af908797ab392bf6
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403810B2

Reaction notes

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