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

HRID 496327ノート

反応式

HRID 496327 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c64543cafc8a43a380437434a76f5899
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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