Imidazole → ((4-Bromothiophen-2-yl)methoxy)(tert-butyl)diphenylsilane

HRID 1363259노트

반응식

HRID 1363259 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][OH:8])[S:5][CH:6]=1.[Si:9](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CN=C1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][O:8][Si:9]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:5][CH:6]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2795484(4-Bromo-2-thienyl)methanol

생성물 1

HCID 59648532((4-Bromothiophen-2-yl)methoxy)(tert-butyl)diphenylsilane수율 101.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a 250-mL round bottom flask fitted with a magnetic stir bar under a N2 atmosphere was added (4-bromothiophen-2-yl)methanol (2.0 g, 10 mmol, 1 equiv) and 30 mL of anhydrous DCM. The reaction mixture was then cooled to 0° C. and the tert-butyl-diphenylsilyl chloride (3.4 g, 3.2 mL, 12.4 mmol, 1.2 equiv) was added followed by imidazole (1.06 g, 15.5 mmol, 1.5 equiv). The reaction was stirred for 16 h and was allowed to equilibrate to rt. The reaction mixture was subsequently taken up in 75 mL DCM and washed with water (100 mL). The organic layer was then dried (Na2SO4), filtered, and evaporated in vacuo. The resulting residue was chromatographed over silica gel (0-10% EtOAc in heptane over 18 min.-retention time (tR) of product: 4-12 min) to give the desired ((4-bromothiophen-2-yl)methoxy)-tert-butyl diphenyl silane (4.3929 g, 98%). 1H-NMR (400 MHz, CD3CN) δ ppm 7.66-7.71 (m, 4H), 7.39-7.51 (m, 6H), 7.29 (d, J=1.46 Hz, 1H), 6.77-6.81 (m, 1H), 4.89 (d, J=0.93 Hz, 2H), 1.06 (s, 9H).

후처리

  1. customTo a 250-mL round bottom flask fitted with a magnetic stir bar under a N2 atmosphere
  2. customto equilibrate to rt
  3. washwashed with water (100 mL)
  4. dry with materialThe organic layer was then dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting residue was chromatographed over silica gel (0-10% EtOAc in heptane over 18 min.-retention time (tR) of product: 4-12 min)

출처 및 근거

ORD 기록
ord-8118d00722aa45c5b1eab7ae6c18cf05
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884124B2

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