2,6-Lutidine → 1-Tosyl-1H-indole-4-carbaldehyde

HRID 1159754

反応式

HRID 1159754 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[C:15]([CH:20]=C)[CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:31].[Na+]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=[O:31])[C:14]=3[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 79372,6-LutidineHCID 124465911-[(4-Methylphenyl)sulfonyl]-4-vinyl-1H-indole2 回HCID 23667635Sodium periodate

生成物 1

HCID 131150931-Tosyl-1H-indole-4-carbaldehyde

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

OsO4 (6 mg, 0.023 mmol) was added to a stirred mixture of 1-[(4-methylphenyl)sulfonyl]-4-vinyl-1H-indole (68 mg, 0.23 mmol; Intermediate 4) and 2,6-lutidine (54 μL, 0.46 mmol) in dioxane (6 mL). The mixture turned from colorless to black in 1 minute. Sodium periodate (0.197 g, 0.92 mmol) in water (1.5 mL, warmed to dissolve) was added. A grey precipitation was immediately formed. The mixture was stirred for 20 min. and partitioned between 2M aqueous HCl (25 mL) and DCM (25 mL). The organic layer was dried, filtered and combined with Intermediate 5 batch 2.

後処理

  1. customblack in 1 minute
  2. customA grey precipitation
  3. customwas immediately formed
  4. custompartitioned between 2M aqueous HCl (25 mL) and DCM (25 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-6975bbe82eba42e4a72b4b46ff4c6e5e
出典データセット
uspto-grants-2010_10
特許番号
US07812017B2

関連ノート

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