3,3-Dimethylbutane-1,2-diol → Ethyl 5-(4-(tert-butyl)-1,3-dioxolan-2-yl)-4-methylisoxazole-3-carboxylate

HRID 1478201

Reaction equation

[CH:1]([C:3]1[O:7][N:6]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]=1[CH3:13])=[O:2].[CH3:14][C:15]([CH3:21])([CH3:20])[CH:16](O)[CH2:17][OH:18]>C1(C)C=CC=CC=1>[C:15]([CH:16]1[CH2:17][O:18][CH:1]([C:3]2[O:7][N:6]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]=2[CH3:13])[O:2]1)([CH3:21])([CH3:20])[CH3:14]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of ethyl 5-formyl-4-methylisoxazole-3-carboxylate (Intermediate C) (50 mg, 0.273 mmol) in toluene (0.5 mL) was added 3,3-dimethylbutane-1,2-diol (32.3 mg, 0.273 mmol) and the mixture was heated at 110° C. for 4.5 hours. The resulting mixture was partitioned between EtOAc and water and the organic layer was dried over MgSO4, filtered and the solvent removed 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

customThe resulting mixture was partitioned between EtOAc and water
dry with materialthe organic layer was dried over MgSO4
filtrationfiltered
customthe solvent removed 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-5b80751ffd1a4ad08adacccadddd3e24
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403810B2

Linked notes

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