Triethyl phosphonoacetate → Ethyl 3-(5,6,7-trimethoxynaphthalen-2-yl)propenoate

HRID 720313ノート

反応式

HRID 720313 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][O:18][C:19]1[C:28]([O:29][CH3:30])=[C:27]([O:31][CH3:32])[CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23]([CH:33]=O)=[CH:24]2>C1COCC1.C(OCC)(=O)C>[CH3:17][O:18][C:19]1[C:28]([O:29][CH3:30])=[C:27]([O:31][CH3:32])[CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23]([CH:33]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:24]2

参加物

6

反応物 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 218916375,6,7-Trimethoxynaphthalene-2-carbaldehyde

生成物 1

HCID 68436859Ethyl 3-(5,6,7-trimethoxynaphthalen-2-yl)propenoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

55% Sodium hydride (241 mg) was suspended in THF (2.5 mL) at −10° C. under an argon atmosphere, a solution of ethyl diethylphosphonoacetate (1.23 g) in THF (5 mL) was added dropwise to the suspension, and the mixture was stirred for 30 minutes. A solution of 5,6,7-trimethoxynaphthalene-2-carboaldehyde (1.23 g) in THF (10 mL) was then added dropwise, and the mixture was stirred for 30 minutes at −10° C. and 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate, washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to obtain the title compound.

後処理

  1. stirringthe mixture was stirred for 30 minutes at −10° C. and 1 hour at room temperature
  2. washwashed with 2 M hydrochloric acid, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

出典と根拠

ORDレコード
ord-09db1d04b4fb45d4926a8b44684d8d97
出典データセット
uspto-grants-2006_11
特許番号
US07135473B2

反応ノート

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