Hydrochloric Acid → HCID 14154277, compound
Reaction equation
[Br:1][C:2]1[C:3]([S:15][CH:16]([CH3:18])[CH3:17])=[C:4]([C:8]2[O:9]CC(C)(C)N=2)[O:5][C:6]=1[Br:7].Cl.C[OH:21].[Li+].[OH-]>O1CCCC1>[Br:1][C:2]1[C:3]([S:15][CH:16]([CH3:18])[CH3:17])=[C:4]([C:8]([OH:9])=[O:21])[O:5][C:6]=1[Br:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 3.01 g (7.58 mmol) of 2-(4,5-dibromo-3-isopropylthio-2-furanyl)-4,4-dimethyloxazoline and aqueous 4N HCl is warmed at reflux under N2 atmosphere for 0.5 hr. The reaction is cooled to 0° C. and treated with methanol (60 mL), tetrahydrofuran (30 mL), and 4.25 g (177.0 mmol) of anhydrous LiOH. The reaction is stirred at 0° C. for 2 hr and 25° C. for 16 hr, then concentrated in vacuo. The resulting residue is dissolved in H2O and extracted with diethyl ether (2X). The aqueous solution is acidified with aqueous 10% HCl and extracted with ethyl acetate (4X). The combined extracts are washed with aqueous saturated NaCl, dried (Na2SO4), and concentrated in vacuo to afford 1.63 g (2.61 g theo.; 62%) of the carboxylic acid as a beige solid. Recrystallization from diethyl ether/hexane affords an analytical sample; mp 130°-131° C.
Workup
- temperatureis warmed
- temperatureat reflux under N2 atmosphere for 0.5 hr
- concentrationconcentrated in vacuo
- dissolutionThe resulting residue is dissolved in H2O
- extractionextracted with diethyl ether (2X)
- extractionextracted with ethyl acetate (4X)
- washThe combined extracts are washed with aqueous saturated NaCl
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b47d9bdf253e4af98751471f05a9b7d9
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04824958
Reaction notes
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