Imidazole → HCID 58367194、化合物

HRID 1891449ノート

反応式

HRID 1891449 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C@@H:6]2[OH:11].[CH3:12][C:13]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C=O)C.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C@@H:6]2[O:11][Si:16]([C:13]([CH3:15])([CH3:14])[CH3:12])([CH3:18])[CH3:17]

参加物

6

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 51915874(S)-4-broMo-2,3-dihydro-1H-inden-1-ol

生成物 1

HCID 58367194HCID 58367194、化合物収率 88%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of (S)-4-bromo-2,3-dihydro-1H-inden-1-ol IND INT-1 (1.56 g, 7.3 mm) in DMF (5 mL) was added TBDMSCl (1.3 g, 8.7 mmol) and imidazole (1.24 g, 18.3 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with saturated NaHCO3 solution (30 mL) and extracted with EA (2×50 mL). The organic layers were washed with water and brine, and dried over MgSO4. The crude product was purified by chromatography (EA/hexane) to afford 2.1 g (88%) of (S)-((4-bromo-2,3-dihydro-1H-inden-1-yl)oxy)(tert-butyl)dimethylsilane IND INT-3 as white solid. LCMS-ESI (m/z) calculated for C15H23BrOSi: 327.3; no M+ observed, tR=5.73 min (Method 2). 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J=7.8 Hz, 1H), 7.22 (d, J=7.4 Hz, 1H), 7.07 (t, J=7.7 Hz, 1H), 5.28 (t, J=7.1 Hz, 1H), 3.00 (ddd, J=16.4, 9.1, 2.9 Hz, 1H), 2.73 (dt, J=16.5, 8.3 Hz, 1H), 2.42 (dddd, J=12.8, 8.0, 7.1, 3.0 Hz, 1H), 1.91 (dtd, J=12.8, 8.9, 7.1 Hz, 1H), 0.98-0.88 (m, 9H), 0.14 (d, J=7.4 Hz, 6H).

後処理

  1. extractionextracted with EA (2×50 mL)
  2. washThe organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe crude product was purified by chromatography (EA/hexane)

出典と根拠

ORDレコード
ord-914c4d7e17d845de81e8708970d6d38f
出典データセット
uspto-grants-2013_08
特許番号
US08507538B2

反応ノート

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