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

HRID 496351노트

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HRID 496351 반응식
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

참가 물질

7

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5bb86cae26ec4ef89bda7f4b16eceb50
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943196B1

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