Acetic Acid → 1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate

HRID 1939717

反応式

HRID 1939717 の反応式
[CH3:1][C:2]([CH3:21])=[CH:3][CH2:4][C@@H:5]([OH:20])[C:6]1[C:16](=[O:17])[C:15]2[C:14]([OH:18])=[CH:13][CH:12]=[C:11]([OH:19])[C:10]=2[C:8](=[O:9])[CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:37](O)(=[O:39])[CH3:38].CCCCCC>CN(C)C1C=CN=CC=1.ClCCl>[C:37]([O:20][CH:5]([C:6]1[C:16](=[O:17])[C:15]2[C:10]([C:8](=[O:9])[CH:7]=1)=[C:11]([OH:19])[CH:12]=[CH:13][C:14]=2[OH:18])[CH2:4][CH:3]=[C:2]([CH3:21])[CH3:1])(=[O:39])[CH3:38]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8058HexaneHCID 10868DicyclohexylcarbodiimideHCID 479503Shikonin

生成物 1

HCID 324641-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate収率 75%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

288 mg (1 mmole) of shikonin, 226 mg (1.1 mmole) of dicyclohexylcarbodiimide and 30 mg (0.25 mmole) of 4-dimethylaminopyridine were dissolved in 3 ml of dry dichloromethane. To the resulting solution was added 60 mg (1 mmole) of acetic acid at 0° C. under nitrogen gas, and the mixture was stirred for 30 minutes and then at room temperature for further 3 hours. 20 ml of n-hexane was added to the reaction solution. The mixture was filtered to remove the insoluble materials. The filtrate was dried and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (n-hexane: ethylacetate=20:1-5:1) to obtain 247 mg (Yield: 75%) of the title compound having the following structure as a red precipitate.

後処理

  1. waitat room temperature for further 3 hours
  2. filtrationThe mixture was filtered
  3. customto remove the insoluble materials
  4. customThe filtrate was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (n-hexane: ethylacetate=20:1-5:1)

出典と根拠

ORDレコード
ord-41a477ecaaf1426e99e718c0c529d573
出典データセット
uspto-grants-1997_12
特許番号
US05696276

関連ノート

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