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

HRID 250531

반응식

HRID 250531 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b180c42e98a940b08668a5b15cdf5683
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863312B2

연결된 노트

불러오는 중…