Water → Methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate

HRID 931487

Reaction equation

C([S:4][CH2:5][C:6]1[N:7]=[C:8]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[O:9][C:10]=1[CH3:11])(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:11][C:10]1[O:9][C:8]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=2)=[N:7][C:6]=1[CH2:5][SH:4]

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of methyl 4-[4-[(acetylsulfanyl)methyl]-5-methyl-1,3-oxazol-2-yl]benzoate (10.5 g, 34.39 mmol, 1.00 equiv) and potassium carbonate (12.3 g, 89.00 mmol, 2.59 equiv) in methanol (200 mL) was stirred at 35° C. under an inert atmosphere of nitrogen for 30 min. Water (200 mL) was added and the resulting solution was extracted with 3×100 mL of dichloromethane. The combined organic layers was washed with 3×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. To afford 8.4 g (93%) of methyl 4-[5-methyl-4-(sulfanylmethyl)-1,3-oxazol-2-yl]benzoate as a white solid. LC-MS-: (ES, m/z): 305 [M+CH3CN+H]+, 264 [M+H]+, 230.

Workup

extractionthe resulting solution was extracted with 3×100 mL of dichloromethane
washThe combined organic layers was washed with 3×50 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-434f5ccddbc84706b88829167ae7c503
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Linked notes

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