Imidazole → tert-Butyl(dimethyl)[(1-pentylprop-2-ynyl)oxy]silane

HRID 250531

反応式

HRID 250531 の反応式
[CH:1]#[C:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C.CCOCC>[C:13]([Si:10]([CH3:12])([CH3:11])[O:9][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:2]#[CH:1])([CH3:16])([CH3:15])[CH3:14]

参加物

6

反応物 3

HCID 795ImidazoleHCID 131661-Octyn-3-olHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 11791325tert-Butyl(dimethyl)[(1-pentylprop-2-ynyl)oxy]silane収率 96%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-octyn-3-ol (5.0 g, 0.039 mol) in DMF (50 mL) were added tert-butyldimethylsilyl chloride (7.16 g, 0.0475 mol) and imidazole (3.2 g, 0.0475 mol). The resulting solution was stirred at RT for 18 h then diluted with ether (200 mL) and washed with water (2×200 mL), saturated solution of NH4Cl (200 mL), and brine (200 mL). The organic solution was dried over sodium sulfate and concentrated in vacuo to afford the desired compound (9.0 g, 95%) as a colorless oil used in the next step without further purification. Rf 0.9 (EtOAc/hexanes 1/9); 1H NMR (CDCl3) δ 0.09 (s, 3H), 0.12 (s, 3H), 0.89 (s, 9H), 0.85-1.00 (t, 3H), 1.20-1.70 (m, 8H), 2.35 (s, 1H), 4.30-4.35 (m, 1H).

後処理

  1. washwashed with water (2×200 mL), saturated solution of NH4Cl (200 mL), and brine (200 mL)
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b180c42e98a940b08668a5b15cdf5683
出典データセット
uspto-grants-2011_01
特許番号
US07863312B2

関連ノート

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