4-Methylpyrimidine → HCID 136375617、化合物

HRID 1296705

反応式

HRID 1296705 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12](OCC)=[O:13].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:8][C:9]1[CH:10]=[C:11]([C:12]([OH:13])=[CH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][N:3]=2)[CH:17]=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 189224-MethylpyrimidineHCID 70785Ethyl 3-chlorobenzoateHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 136375617HCID 136375617、化合物収率 96.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cold (0° C.) solution of 4-methylpyrimidine (4.56 mL 50.1 mmol) and ethyl 3-chlorobenzoate (7.90 mL 50.1 mmol) in tetrahydrofuran (50 mL) was added lithium bis(trimethylsilyl)amide (100 mL, 1.0M in tetrahydrofuran, 100 mmol) dropwise over 30 minutes. The resultant mixture was warmed to room temperature and stirred 16 hours. The reaction mixture was concentrated in vacuo. The resultant oil was diluted with methanol. Upon standing, a solid precipitated, which was collected on a filter to provide 1-(3-chlorophenyl)-2-(4-pyrimidinyl)ethenol (11.2 g, 93%) as a yellow solid. Rf 0.31 (3:1 hexanes:ethyl acetate); 1H NMR (d6-DMSO) δ 8.37 (s, 1H), 7.98 (m, 1H), 7.81–7.76 (m, 2H), 7.38–7.32 (m, 2H), 6.71 (br, 1H), 5.65 (s, 1H); MS m/z 233 (M+1).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe resultant oil was diluted with methanol
  3. customa solid precipitated
  4. customwhich was collected on
  5. filtrationa filter

出典と根拠

ORDレコード
ord-e771dfcbc4ea444089d4ba7654147751
出典データセット
uspto-grants-2007_07
特許番号
US07247626B2

関連ノート

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