Sodium Hydroxide → HCID 86748115, compound
Reaction equation
C([O:3][C:4](=[O:28])/[C:5](=[N:25]/[O:26][CH3:27])/[C:6]1[S:7][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:9][CH:10]=1)C.[OH-].[Na+]>CO.O1CCCC1>[CH3:27][O:26]/[N:25]=[C:5](\[C:6]1[S:7][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:9][CH:10]=1)/[C:4]([OH:28])=[O:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
(Z)-alpha-(methoxyimino)-5-[2-(2-naphthalenyloxy)ethoxy]-2-thiopheneacetic acid ethyl ester (0.2 g) in methanol (2 mL) and tetrahydrofuran (2 mL) was treated with 3N sodium hydroxide (0.5 mL) and the stirred mixture was heated at 50° C. for 30 minutes. After the solvents were removed in vacuo, the concentrate was diluted with water (10 mL), acidified with 1N hydrochloric acid (3 mL) and extracted with dichloromethane (2×10 mL). The combined organic layers were washed with brine, dried (MgSO4) and evaporated. The resulting solid was crystallized from dichloromethane-hexane to provide 0.157 g of (Z)-alpha-(methoxyimino)-5-[2-(2-naphthalenyloxy)ethoxy]-2-thiopheneacetic acid as its hernihydrate, mp 118°-120° C.
Workup
- customAfter the solvents were removed in vacuo
- additionthe concentrate was diluted with water (10 mL)
- extractionextracted with dichloromethane (2×10 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- customevaporated
- customThe resulting solid was crystallized from dichloromethane-hexane
Sources & evidence
- ORD record
- ord-c26fbf492ab148c0a8cbf41fee838f4d
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344843
Reaction notes
Loading…