Tetrahydrofuran → 3-(4-Nitro-pyridin-2-ylmethylene)-3H-isobenzofuran-1-one

HRID 600265ノート

反応式

HRID 600265 の反応式
COP([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])NN=1)(=O)OC.[N+:18]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH:27]=O)[CH:22]=1)([O-:20])=[O:19].C(N(CC)CC)C.C1C[O:39]CC1>O>[N+:18]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH:27]=[C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7](=[O:39])[O:17]2)[CH:22]=1)([O-:20])=[O:19]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 145789294-NitropicolinaldehydeHCID 86628633(4-Oxo-3,4-dihydro-phthalazin-1-yl)-phosphonic acid dimethyl ester

生成物 1

HCID 689120253-(4-Nitro-pyridin-2-ylmethylene)-3H-isobenzofuran-1-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a cooled solution of (4-oxo-3,4-dihydro-phthalazin-1-yl)-phosphonic acid dimethyl ester (0.202 g, 0.837 mmol) in THF (4 mL) at 10° C. was added 4-nitro-pyridine-2-carbaldehyde (0.837 mmol) under a nitrogen atmosphere. Triethylamine (0.174 mL, 1.25 mmol) was added dropwise over 10 minutes and then allowed to stir at room temperature for 18 hours. The yellow suspension was poured in water (9 mL), and the then filtered, the solid was washed with water (2×2 mL), hexane (2×2 mL) and then diethyl ether (2×2 mL) and then dried in vacuo to afford a 0.73 g of the desired products. Two peaks in LC-MS analysis, (0.13 g, 18% two steps) and required no further purification, m/z (LC-MS, ESP), RT=4.26 mins (M+H) 269, & RT=4.52 mins (M+H) 269.

後処理

  1. filtrationthe then filtered
  2. washthe solid was washed with water (2×2 mL), hexane (2×2 mL)
  3. dry with materialdiethyl ether (2×2 mL) and then dried in vacuo

出典と根拠

ORDレコード
ord-af046cb2823e4619bf45a8f2c7832825
出典データセット
uspto-grants-2011_03
特許番号
US07902193B2

反応ノート

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