HRID464461

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID9837437

(S)-2-Hydroxy-2-(3-phenoxyphenyl)acetonitrile

C14H11NO2

$结构：CC1(C)[C@H](C(=O)O)[C@@H]1/C=C\C(=O)OC1CCC1$

HCID70477467

未命名化合物

PRODUCTS

生成物

HCID21881879

未命名化合物

$结构：CC1(C)[C@H](C(=O)O[C@H](C#N)c2cccc(Oc3ccccc3)c2)[C@@H]1/C=C\C(=O)OC1CCC1$

HCID131713082

未命名化合物

收率 178.3%

PROCEDURE

实验过程

Using the procedure of Step A above, 1.8 g of the acid of Step B and 2 g of (S)α-cyano-3-phenoxy-benzyl alcohol were reacted and the product was chromatographed over silica gel. Elution with a 9-1 cyclohexane-ethyl acetate mixture and then with an 8-2 n-hexane-isopropyl ether mixture yielded 3.0 g of (S)α-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[Z-2-(cyclobutoxycarbonyl)-ethenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+45.5°±2° (c=0.6% in chloroform).

WORKUP

后处理

customthe product was chromatographed over silica gel
washElution with a 9-1 cyclohexane-ethyl acetate mixture

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3dcc9229ad294d1a88625bb0825a4847
来源数据集: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04547522
来源说明: uspto-grants-1985_10

反应 SMILES

[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[O:8])[C@H:3]1[C:14]([OH:16])=[O:15].[C:18]([C@@H:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1)#[N:19]>>[CH3:14][CH2:3][CH2:2][CH2:4][CH2:5][CH3:6].[CH:23]([O:27][CH:28]([CH3:33])[CH3:29])([CH3:24])[CH3:22].[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13]2)=[O:8])[C@H:3]1[C:14]([O:16][C@H:20]([C:18]#[N:19])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:22]=1)=[O:15]