Imidazole → HCID 59027527, 화합물

HRID 41133

반응식

HRID 41133 반응식
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[C:25]([CH:27]=1)[OH:26].N1C=CN=C1>CN(C=O)C.O>[CH3:19][O:20][C:21]1[CH:27]=[C:25]([O:26][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=[C:23]([OH:28])[CH:22]=1

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 71648FlamenolHCID 94078tert-Butyldiphenylchlorosilane

생성물 1

HCID 59027527HCID 59027527, 화합물수율 33%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

tert-Butyldiphenylsilylchloride (TBDPSCl) (1.8 mL, 1.96 g, 7.14 mmol) was added to a suspension of 5-methoxyresorcinol 18 (1.0 g, 7.14 mmol) and imidazole (729 mg, 10.71 mmol) in dry DMF (5 mL) under argon at −22° C. and the mixture was stirred for 10 min. The reaction mixture was diluted with H2O (25 mL) and extracted with EtOAc (3×25 mL). The combined organic extracts were washed with aq 1M of HCl (2×25 mL), and brine (2×25 mL). The organic layer was then dried (Na2SO4) and concentrated in vacuo. The crude silyl phenol 19 was purified by FCC on silica gel (5% ethyl acetate in hexane) to afford pure silyl phenol 19 (892 mg, 33%): 1H NMR (300 MHz, CDCl3) δ 7.89-7.75 (4H, m, HAr), 7.48-7.34 (6H, m, HAr), 5.98 (2H, t, J=2.1 Hz, HAr), 5.92 (1H, t, J=2.1 Hz, HAr), 5.13 (1H, br, s, HO—), 3.56 (3H, s, H3CO), 1.14 (9H, s, [(H3C)3C]; 13C NMR (75 MHz, CDCl3) δ 161.1, 157.3, 156.8, 135.4, 132.8, 129.9, 127.7, 100.1, 98.5, 95.0, 55.0, 26.4, 19.4; LRMS (CI), m/z (relative intensity): 378([M+1]+, 30), 321 (100), 243 (30), 213 (10), 199 (29). This material was employed directly in the next step.

후처리

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe combined organic extracts were washed with aq 1M of HCl (2×25 mL), and brine (2×25 mL)
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude silyl phenol 19 was purified by FCC on silica gel (5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-69ea5fcdb2f84d7c8f92d66bcf1f07b7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530512B2

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