Diisopropylamine → HCID 178458806、化合物

HRID 2075717ノート

反応式

HRID 2075717 の反応式
N(C(C)C)C(C)C.C([Li])CCC.[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[SH:18].[F:19][C:20]([F:26])([F:25])[C:21](=[O:24])[CH2:22][CH3:23]>C1COCC1>[F:19][C:20]([F:26])([F:25])[C:21]([C:17]1[S:13][C:14]([SH:18])=[N:15][CH:16]=1)([OH:24])[CH2:22][CH3:23]

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 2382881,1,1-Trifluorobutan-2-oneHCID 178418339ButyllithiumHCID 178527881HCID 178527881、化合物

生成物 1

HCID 178458806HCID 178458806、化合物

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

iPr2NH (2.0 g, 19.9 mmol) was dissolved in THF (23 mL) and cooled to −78° C. n-Butyllithium (2.5M, 8.0 mL, 19.9 mmol) was added dropwise, followed by thiazole-2-thiol (0.9 g, 7.9 mmol) in THF (5 mL). After 10 minutes, trifluoro-2-butanone (0.5 g, 4.0 mmol) was added and the reaction was stirred at −78° C. for 6 hours. The reaction was warmed to room temperature and quenched with 5% aqueous NH4Cl (20 mL). The aqueous layer was acidified and extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (50% EtOAc in hexanes) to give the desired product, 10b.

後処理

  1. additionwas added dropwise
  2. temperatureThe reaction was warmed to room temperature
  3. customquenched with 5% aqueous NH4Cl (20 mL)
  4. extractionextracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (50% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-336bc8768f0a4388b092edd8a08237d4
出典データセット
uspto-grants-2011_04
特許番号
US07919621B2

反応ノート

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