盐酸 → 3-(ethoxycarbonyl)-8-methyl-2-(trifluoromethyl)-2H-chromene-6-carboxylic acid

HRID 855110笔记

反应方程式

HRID 855110 反应方程式
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH3:13])[C:11]=1[OH:12])[C:6]([OH:8])=[O:7])=O.C([O-])([O-])=O.[K+].[K+].C(N(CC)CC)C.[F:27][C:28]([F:37])([F:36])/[CH:29]=[CH:30]/[C:31]([O:33][CH2:34][CH3:35])=[O:32].Cl>CS(C)=O.CC(C)=O>[CH2:34]([O:33][C:31]([C:30]1[CH:29]([C:28]([F:27])([F:36])[F:37])[O:12][C:11]2[C:3]([CH:1]=1)=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:9][C:10]=2[CH3:13])=[O:32])[CH3:35]

参与物

8

反应物 5

HCID 313盐酸HCID 8471三乙胺HCID 11430碳酸钾HCID 53712614,4,4-三氟巴豆酸乙酯HCID 865994903-甲酰基-4-羟基-5-甲基苯甲酸

产物 1

HCID 695174193-(ethoxycarbonyl)-8-methyl-2-(trifluoromethyl)-2H-chromene-6-carboxylic acid

试剂、催化剂与溶剂 2

HCID 180丙酮溶剂HCID 679二甲基亚砜溶剂

反应条件

温度
90 °C

实验过程

A mixture of 3-formyl-4-hydroxy-5-methylbenzoic acid (8.8 g, 48.89 mmole), K2CO3 (13.49 g, 97.78 mmole), triethylamine (19.79 g, 195.56 mmole), and ethyl 4,4,4-trifluorocrotonate (32.85 g, 195.56 mmole) in anhydrous DMSO (20.0 mL) was heated to 90° C. under a dry N2 atmosphere for 18 hrs. The mixture was then cooled, poured into 2.0 N HCl (100 ml), and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated in vacuo to give an oily solid. Redissolved in acetone to givea white precipitat, which was filtered and dried on high vacuum (7.2 g, 51%). GCMS m/z 330.0 (M+). 1H NMR (DMSO/400 MHz) 12.99 (s, 1H), 8.11 (s, 1H), 8.06 (s, 1H), 7.94 (s, 1H), 6.19 (q, 1H, J=7.0 Hz), 4.35 (m, 2H), 2.31 (s, 3H), 1.36 (m, 3H).

后处理

  1. temperatureThe mixture was then cooled
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined extracts were washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an oily solid
  8. filtrationwas filtered
  9. customdried on high vacuum (7.2 g, 51%)

来源与证据

ORD记录
ord-0ed30349f05e423aa02780fb30775c83
来源数据集
uspto-grants-2007_08
专利号
US07259266B2

反应笔记

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