Hydrochloric Acid → 2-[4-(3-Hydroxypropyl)naphthyl]dioxolane

HRID 1166745ノート

反応式

HRID 1166745 の反応式
C([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]2[O:22][CH2:21][CH2:20][O:19]2)=[CH:10][CH:9]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.O>[OH:3][CH2:4][CH2:6][CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]2[O:19][CH2:20][CH2:21][O:22]2)=[CH:10][CH:9]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 545306942-[4-(2-Ethoxycarbonylethyl)naphthyl]dioxolane

生成物 1

HCID 538626532-[4-(3-Hydroxypropyl)naphthyl]dioxolane収率 37.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of 2-[4-(2-ethoxycarbonylethyl)naphthyl]dioxolane (210 mg, 0.70 mmol) in anhydrous THF (5 mL) was added at 0° C. 1M lithium aluminum hydride in THF (0.5 mL). THF (5 mL) was added and the mixture was stirred at room temperature for 16 hr, diluted with water (10 mL), acidified with conc. hydrochloric acid, and extracted with ether (3×10 mL). The combined organic extracts were dried (MgSO4), and concentrated. The residue was purified by flash chromatography using hexane/ethyl acetate 2:1 as eluent to provide 67 mg (37%) of a colorless oil.

後処理

  1. extractionextracted with ether (3×10 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-bc54e2d00eaf49c9ac6d1b10b491e0a4
出典データセット
uspto-grants-2003_09
特許番号
US06613942B1

反応ノート

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