Ammonium Chloride → 4-[hydroxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]benzoic Acid Methylester

HRID 496351ノート

反応式

HRID 496351 の反応式
C[Li].[CH3:3]COCC.[OH:8][CH:9]([C:19]1[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([O:28][CH3:29])=[C:21]([O:30][CH3:31])[C:20]=1[O:32][CH3:33])[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1.COC1C(OC)=C(OC)C(OC)=C(C)C=1C=O.[Cl-].[NH4+]>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[CH3:3][O:15][C:14](=[O:16])[C:13]1[CH:12]=[CH:11][C:10]([CH:9]([OH:8])[C:19]2[C:24]([CH3:25])=[C:23]([O:26][CH3:27])[C:22]([O:28][CH3:29])=[C:21]([O:30][CH3:31])[C:20]=2[O:32][CH3:33])=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehydeHCID 223252814-[Hydroxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]benzoic acidHCID 178467906HCID 178467906、化合物

生成物 1

HCID 867598454-[hydroxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]benzoic Acid Methylester収率 33%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To a solution of zinc chloride (1.91 mmol) in dry tetrahydrofuran (9.6 ml) was added under ice-cooling a 1.4 M methyllithium/ether solution (4.1 ml, 5.73 mmol), and the mixture was stirred at 0° C. for 30 minutes. The reaction mixture was cooled to −78° C., to which was added a solution of the compound (500 mg, 1.91 mmol) obtained in Step 1 in dry tetrahydrofuran (2.0 ml) and the mixture was further stirred at −78° C. for 4 hours. Subsequently, a solution of 2,3,4,5-tetramethoxy-6-methylbenzaldehyde (1.38 g, 5.73 mmol) in dry tetrahydrofuran (2 ml) was added and the mixture was stirred overnight at room temperature. To the reaction mixture an aqueous solution of saturated ammonium chloride (2.5 ml) was added at 0° C. After concentrating under reduced pressure, the concentrate was diluted with water and extracted three times with chloroform. After the organic layer was dried, the solvent was distilled off. After purification by a silica gel column chromatography (ethyl acetate : hexane=1:2), the title compound (237 mg, 0.63 mmol, yield 33%) was obtained.

後処理

  1. temperatureThe reaction mixture was cooled to −78° C., to which
  2. stirringthe mixture was further stirred at −78° C. for 4 hours
  3. stirringthe mixture was stirred overnight at room temperature
  4. concentrationAfter concentrating under reduced pressure
  5. additionthe concentrate was diluted with water
  6. extractionextracted three times with chloroform
  7. customAfter the organic layer was dried
  8. distillationthe solvent was distilled off
  9. customAfter purification by a silica gel column chromatography (ethyl acetate : hexane=1:2)

出典と根拠

ORDレコード
ord-5bb86cae26ec4ef89bda7f4b16eceb50
出典データセット
uspto-grants-2005_09
特許番号
US06943196B1

反応ノート

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