Diethyl Ether → 2-(2-(Benzyloxy)ethyl)-1,3-dioxolane

HRID 1733775ノート

反応式

HRID 1733775 の反応式
[OH:1][CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)C>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:11]([O:1][CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2319712-(1,3-Dioxolan-2-yl)ethan-1-ol

生成物 1

HCID 194385412-(2-(Benzyloxy)ethyl)-1,3-dioxolane

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

2-(2-Hydroxyethyl)-1,3-dioxolane (7.0 g, 58.3 mmol) was dissolved in dried tetrahydrofuran (distilled from sodium) (200 ml). Sodium hydride (2.0 g, 66.7 mmol, 80%) was added and the mixture was stirred at ambient temperature until gas evolution was completed. Tetrabutylammonium iodide (0.22 g, 0.6 mmol) and benzyl bromide (9.7 g, 56.8 mmol) were added, and the mixture was stirred for 24 hours at ambient temperature. Diethyl ether (100 ml) was added and the mixture was washed with water (3×100 ml), dried with magnesium sulphate and 2-(2-benzyloxyethyl)-1,3-dioxolane was distilled as a colourless oil. Yield 9.3 g (75%) b.p. 75°-78° C. (0.02 mm Hg). The structure was confirmed by 1H NMR and 13C NMR.

後処理

  1. stirringthe mixture was stirred for 24 hours at ambient temperature
  2. washthe mixture was washed with water (3×100 ml)
  3. dry with materialdried with magnesium sulphate and 2-(2-benzyloxyethyl)-1,3-dioxolane
  4. distillationwas distilled as a colourless oil

出典と根拠

ORDレコード
ord-eb024837b17349ed9b3ad432f1d88ac4
出典データセット
uspto-grants-1996_07
特許番号
US05531978

反応ノート

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