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Methyl (trimethylsilyl)acetate → Methyl 3-(oxazol-2-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

HRID 2375742
ノート
印刷プレビュー

反応式

HRID 2375742 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si]([CH2:15][C:16]([O:18][CH3:19])=[O:17])(C)C.[O:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)=[CH:29][CH:28]=1)=O>C1COCC1>[O:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]([C:27]1[CH:28]=[CH:29][C:30]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)=[CH:31][CH:32]=1)=[CH:15][C:16]([O:18][CH3:19])=[O:17]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 76210Methyl (trimethylsilyl)acetateHCID 2733832Lithium hexamethyldisilazaneHCID 59855138Oxazol-2-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanone

生成物 1

HCID 69142498Methyl 3-(oxazol-2-yl)-3-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)acrylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Lithium bis(trimethylsilyl)amide (3.46 mmol, 1M in THF) was added dropwise to a solution of methyl trimethylsilylacetate (3.46 mmol) in THF (5 mL) at −78° C. After 20 minutes at −78° C., a solution of 10.2 (2.16 mmol) in THF (9 mL) was added dropwise and the reaction was maintained at −78° C. for 1.5 hours. The reaction was quenched with water and extracted with EtOAc. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed (silica gel, 1:1 EtOAc/hexane) to afford compound 10.3. MS ESI (pos.) m/e 330.1 (M+1).

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (silica gel, 1:1 EtOAc/hexane)

出典と根拠

ORDレコード
ord-9c43854d0d8344388626969d8e98f312
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07465804B2

反応ノート

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