HRID1161096

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11776

Triphenylphosphine

C18H15P

HCID5363146

Diisopropyl azodicarboxylate

C8H14N2O4

HCID57438294

未命名化合物

结构：N#Cc1cccc(C(OC2CCCCO2)c2ccc(CO)cc2)c1

HCID57438299

未命名化合物

PRODUCTS

生成物

结构：CC(=O)c1ccc(OCc2ccc(C(OC3CCCCO3)c3cccc(C#N)c3)cc2)c(Cl)c1O

HCID57884499

未命名化合物

收率 98.6%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

Add diisopropylazodicarboxylate (DIAD, 5.418 g, 26.80 mmol) to a solution of 1-(3-chloro-2,4-dihydroxy-phenyl)ethanone (5.000 g, 26.80 mmol), 3-[(4-hydroxymethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (8.666 g, 26.80 mmol), and triphenylphosphine (7.028 g, 26.80 mmol) in tetrahydrofuran (0.200M) at 0° C. Stir for 2 hours while warming to room temperature. Add silica gel and evaporate solvent. Chromatograph with Biotage Flash 75, eluting with 50-90% ethyl acetate/hexanes to afford the title compound as a white solid (13.00 g, 26.42 mmol, 98%): MS (m/z): 490 (M−H).

WORKUP

后处理

customAdd silica gel and evaporate solvent
washChromatograph with Biotage Flash 75, eluting with 50-90% ethyl acetate/hexanes

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-224f780b7dfb420aab9a31e7d8c7ef2f
来源数据集: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07816523B2
来源说明: uspto-grants-2010_10

反应 SMILES

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:15][C:16]1[C:17]([OH:26])=[C:18]([C:23](=[O:25])[CH3:24])[CH:19]=[CH:20][C:21]=1[OH:22].O[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([O:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][O:46]2)[C:36]2[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=2)[C:39]#[N:40])=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:23]([C:18]1[CH:19]=[CH:20][C:21]([O:22][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([CH:35]([O:44][CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][O:46]3)[C:36]3[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=3)[C:39]#[N:40])=[CH:33][CH:34]=2)=[C:16]([Cl:15])[C:17]=1[OH:26])(=[O:25])[CH3:24]