HRID1070196

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID887

Methanol

CH4O

HCID14797

Potassium hydroxide

HKO

$结构：COC(=O)C(C)(C)CCC/C(=N\OCc1ccc(OCc2nc(-c3ccccc3)oc2C)cc1)c1ccccc1$

HCID11145964

未命名化合物

PRODUCTS

生成物

$结构：Cc1oc(-c2ccccc2)nc1COc1ccc(CO/N=C(\CCCC(C)(C)C(=O)O)c2ccccc2)cc1$

HCID11005907

未命名化合物

收率 83%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A 4N aqueous solution of potassium hydroxide (5 ml) was added to a solution of methyl E-2,2-dimethyl-6-[4(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-6-phenylhexanoate (340 mg) in tetrahydrofuran (5 ml)-methanol (5 ml), which was heated to reflux for 2 hours and cooled to room temperature. Dilute hydrochloric acid was added to the reaction mixture to neutralize and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain E-2,2-dimethyl-6-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-6-phenylhexanoic acid (275 mg, yield 83%) as colorless crystals. m.p. 111-112° C.

WORKUP

后处理

temperaturewas heated
temperatureto reflux for 2 hours
extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
dry with materialdried (MgSO4)
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ec8278887ffe4b328047d71bd7b835b4
来源数据集: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06251926B1
来源说明: uspto-grants-2001_06

反应 SMILES

[OH-].[K+].[CH3:3][C:4]([CH3:42])([CH2:9][CH2:10][CH2:11]/[C:12](=[N:19]\[O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[CH:24][CH:23]=1)/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]([O:7]C)=[O:6].CO.Cl>O1CCCC1>[CH3:3][C:4]([CH3:42])([CH2:9][CH2:10][CH2:11]/[C:12](=[N:19]\[O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[CH:26][CH:27]=1)/[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:5]([OH:7])=[O:6]