tert-butyl-7-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]chromane-3-carboxylate → HCID 11268964, compound

HRID 268697Notes

Reaction equation

C([O:5][C:6]([CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:18][CH2:19][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:24][C:25]=3[CH3:26])=[CH:14][CH:15]=2)[O:10][CH2:9]1)=[O:7])(C)(C)C>C(O)=O>[CH3:26][C:25]1[O:24][C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:22][C:21]=1[CH2:20][CH2:19][O:18][C:13]1[CH:12]=[C:11]2[C:16]([CH2:17][CH:8]([C:6]([OH:7])=[O:5])[CH2:9][O:10]2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

tert-butyl-7-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]chromane-3-carboxylate (5.2 g, 11.95 mmol) was dissolved in 25 ml of formic acid and heated at 60° C. for 12 hrs. Formic acid was removed in vacuum pump and ether (25 ml) was added and heated for 10 minutes. The resultant suspension was cooled at −20° C. for 1 hr and filtered. The solid product was washed with 20 ml of diethyl ether and dried to give the compound 7-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]chromane-3-carboxylic acid as white powder (3.8 g, 84%).

Workup

customFormic acid was removed in vacuum pump and ether (25 ml)
additionwas added
temperatureheated for 10 minutes
temperatureThe resultant suspension was cooled at −20° C. for 1 hr
filtrationfiltered
washThe solid product was washed with 20 ml of diethyl ether
customdried

Sources & evidence

ORD record: ord-114603fe5d4046e3b2e0a4d58c1ce1a1
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446127B2

Reaction notes

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