Water → 2-{4-[Hydroxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]phenyl}-1,3-dioxolane

HRID 496327노트

반응식

HRID 496327 반응식
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[C:8]([O:15][CH3:16])=[C:7]([CH3:17])[C:4]=1[CH:5]=[O:6].Br[C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[O:29][CH2:28][CH2:27][O:26]2)=[CH:21][CH:20]=1.[Mg].O>C1COCC1>[OH:6][CH:5]([C:4]1[C:7]([CH3:17])=[C:8]([O:15][CH3:16])[C:9]([O:13][CH3:14])=[C:10]([O:11][CH3:12])[C:3]=1[O:2][CH3:1])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[O:26][CH2:27][CH2:28][O:29]2)=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 27738422-(4-Bromophenyl)-1,3-dioxolaneHCID 5462224MagnesiumHCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehyde

생성물 1

HCID 223253012-{4-[Hydroxy-(2,3,4,5-tetramethoxy-6-methylphenyl)methyl]phenyl}-1,3-dioxolane수율 96%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice-cold solution of 2,3,4,5-tetramethoxy-6-methylbenzaldehyde (5.03 g, 20.94 mmol) in THF (200 ml) was added dropwise a Grignard reagent prepared from 2-(4-bromophenyl)-1,3-dioxolane (12.0 g, 52.4 mmol) and magnesium (1.40 g, 57.6 mmol), and then stirred at room temperature for 4 hours. The reaction mixture was poured into water and was extracted with ether. After the extract was washed with water and dried, and then the solvent was distilled off. The residue was purified by a silica gel column chromatography (hexane:ethyl acetate=3:1) to yield the title compound (7.80 g, 20.0 mmol, yield 96%).

후처리

  1. extractionwas extracted with ether
  2. washAfter the extract was washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by a silica gel column chromatography (hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-c64543cafc8a43a380437434a76f5899
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943196B1

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