HRID1513947

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID21226445

未命名化合物

结构：O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc(F)cc2F)ccc2cc(O)ccc12

HCID67004951

未命名化合物

PRODUCTS

生成物

结构：Oc1ccc2c(C(O)c3ccc(OCCN4CCCCC4)cc3)c(-c3ccc(F)cc3F)ccc2c1

HCID67004725

未命名化合物

收率 102.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

Dissolve [2-(2,4-difluoro-phenyl)-6-hydroxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (3.3 g, 6.8 mmol) in dry THF (100 mL) and stir under nitrogen. Slowly add lithium aluminum hydride (0.9 g, 24 mmol) and heat to reflux. Cool to room temperature after 30 minutes and quench excess LiAlH4 with slow addition of ice. Dilute with water and adjust the pH to 7 with 1M HCl. Extract five times with 20% IPA in chloroform. Dry the combined organic layers with sodium sulfate, filter and concentrate in vacuo to yield 3.4 g (100%) of the title compound.

WORKUP

后处理

customquench excess LiAlH4
additionwith slow addition of ice
additionDilute with water
extractionExtract five times with 20% IPA in chloroform
dry with materialDry the combined organic layers with sodium sulfate
filtrationfilter
concentrationconcentrate in vacuo

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-bf4394cc6f0f40d1a63dfdf56f2508f9
来源数据集: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08217032B2
来源说明: uspto-grants-2012_07

反应 SMILES

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[C:10]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:24][CH:23]=1)=[O:21].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH:20]([OH:21])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:24][CH:23]=2)=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]2