四氢呋喃 → (1R*,2R*)-Acetic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester

HRID 28792笔记

反应方程式

HRID 28792 反应方程式
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].Cl.C(N([CH2:12][CH3:13])CC)C.[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[OH:17][C@@H:16]1[C:12]2[C:13](=[CH:18][CH:14]=[CH:15][CH:16]=2)[CH:18]=[CH:14][C@H:15]1[O:3][C:1](=[O:4])[CH3:2]

参与物

5

反应物 3

HCID 8028四氢呋喃HCID 11130三乙胺盐酸盐HCID 517045醋酸钠

产物 1

HCID 9837127(1R*,2R*)-Acetic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester

试剂、催化剂与溶剂 1

HCID 6359561,1'-双(二苯基膦)二茂铁催化剂

实验过程

To a flame dried round bottom flask, [Rh(COD)Cl]2 (4.3 mg, 0.008 mmol DPPF (9.6 mg, 0.017 mmol),1 (50 mg, 1.39 mmol), and sodium acetate (142 mg, 1.74 mmol) were added followed by addition of THF (2 mL) and triethylamine hydrochloride (239 mg, 1.74 mmol). The mixture was heated at reflux for 3 hours and the solvents were removed in vacuio. The resulting mixture was purified by flash chromatography (30% ethyl acetate in hexanes) to give 2 as a crystalline solid (41 mg), 63%). Rf=0.26 on silica gel (20% ethyl acetate:hexanes); mp 67-68° (Et2O); IR (KBr, cm−1) 1H NMR (400 MHz, CDCl3) δ 7.54-7.53 (1H, m), 7.29-7.24 (2H, m), 7.10-7.08 (1H, m), 6.50 (1H, dd, J=3.9, 1.3 Hz), 5.85 (1H, dd, J=9.9, 3.1 Hz), 5.59 (1H, ddd, J=9.0, 2.8, 1.9 Hz), 4.92 (1H, d, J=9.0 Hz), 2.64 (1H, s), 2.12 (3H, s); 13C NMR (400 MHz, CDCl3) δ 171.3, 135.2, 131.5, 129.5, 128.3, 126.7, 126.0, 125.4, 75.3, 71.7, 21.2. HRMS calcd for C12H12O3 (M+): 204.0786. Found: 204.0791.

后处理

  1. customTo a flame dried round bottom flask
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 3 hours
  4. customthe solvents were removed in vacuio
  5. customThe resulting mixture was purified by flash chromatography (30% ethyl acetate in hexanes)

来源与证据

ORD记录
ord-88e7ded5a61e46328892f889f67ed6cb
来源数据集
uspto-grants-2008_09
专利号
US07420003B2

反应笔记

加载中…