HRID1830513

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(Cc2ccccc2O)ccc2cc(O)ccc12

HCID9982673

未命名化合物

HCID21226445

未命名化合物

PRODUCTS

生成物

结构：Oc1ccc2c(C(O)c3ccc(OCCN4CCCCC4)cc3)c(Cc3ccccc3O)ccc2c1

HCID10050985

未命名化合物

收率 82%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

Add LAH solution (0.3 mL, 1M/THF) to a solution of [6-hydroxy-2-(2-hydroxy-benzyl)-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (150 mg, 0.31 mmol) in THF (3 mL) at r.t. Stir for 30 min and quench with aq. NaHCO3. Dilute with CH2Cl2, wash with water and brine, dry over MgSO4, filter and concentrate. Purify the crude product by flash chromatography (0–5% (2M NH3 in MeOH)/CH2Cl2) to afford 6-(2-hydroxy-benzyl)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-naphthalen-2-ol (123 mg, 82%).

WORKUP

后处理

customquench with aq. NaHCO3
additionDilute with CH2Cl2
washwash with water and brine
dry with materialdry over MgSO4
filtrationfilter
concentrationconcentrate
customPurify the crude product by flash chromatography (0–5% (2M NH3 in MeOH)/CH2Cl2)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-89abcd28db0a4927804de3b3e6ce51b6
来源数据集: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07067510B2
来源说明: uspto-grants-2006_06

反应 SMILES

[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:22][CH:21]=1)=[O:19])=[C:13]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[OH:42])[CH:12]=[CH:11]2>C1COCC1>[OH:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[CH2:35][C:13]1[C:14]([CH:18]([OH:19])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:22][CH:21]=2)=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:7])[CH:17]=[CH:16]2