Potassium Acetate → Methyl 4-(acetyloxy)-2-methyl-1-benzofuran-6-carboxylate

HRID 2233361ノート

反応式

HRID 2233361 の反応式
[CH3:1][O:2][C:3](/[C:5](=[CH:10]/[C:11]1[O:12][C:13]([CH3:16])=[CH:14][CH:15]=1)/[CH2:6][C:7]([OH:9])=O)=[O:4].[C:17]([O-])(=[O:19])[CH3:18].[K+].O.C(OCC)(=O)C>C(OC(=O)C)(=O)C>[CH3:16][C:13]1[O:12][C:11]2[CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=[C:7]([O:9][C:17](=[O:19])[CH3:18])[C:15]=2[CH:14]=1

参加物

5

反応物 3

HCID 517044Potassium AcetateHCID 22728543Water ethylacetateHCID 60145978HCID 60145978、化合物

生成物 1

HCID 53249530Methyl 4-(acetyloxy)-2-methyl-1-benzofuran-6-carboxylate

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

反応条件

温度
140 °C

実験手順

A mixture of E-3-methoxycarbonyl-4-(5-methylfur-2-yl)-but-3-enoic acid (Method 15; 1.39 g, 6.2 mmol) and potassium acetate (620 mg, 6.3 mmol) in acetic anhydride (12.5 ml) was heated at 140° C. for 15 mins. The reaction mixture was cooled and poured on to a water/ethyl acetate mixture; the aqueous layer was separated and the organic layer washed sequentially with saturated sodium bicarbonate solution and brine, dried (MgSO4) and evaporated in vacuo to yield the crude product as a dark crystalline mass. This was chromatographed (50 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%) to give the title compound as a pale yellow solid, 1.42 g (92%). NMR: 2.36 (s, 3H), 3.34 (s, 3H), 3.87 (s, 3H), 6.68 (s, 1H), 7.56 (s, 1H), 7.96 (s, 1H); m/z 247 (M−H)−, 97.1% by LC-MS.

後処理

  1. temperatureThe reaction mixture was cooled
  2. customthe aqueous layer was separated
  3. washthe organic layer washed sequentially with saturated sodium bicarbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto yield the crude product as a dark crystalline mass
  7. customThis was chromatographed
  8. wash(50 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%)

出典と根拠

ORDレコード
ord-6cca5735a1ac41599c822c4cb0f4dad8
出典データセット
uspto-grants-2010_05
特許番号
US07709505B2

反応ノート

読み込み中…