Hexane → HCID 59394508、化合物

HRID 45154ノート

反応式

HRID 45154 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li][CH2:15]CCC.CCCCCC.C([O:27][C:28](=O)[C:29]([F:32])([F:31])[F:30])C>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[C:11]([C:28]([OH:27])([CH3:15])[C:29]([F:32])([F:31])[F:30])[N:10]([CH3:13])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 8058HexaneHCID 9794Ethyl trifluoroacetateHCID 132489953-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazoleHCID 178418339Butyllithium

生成物 1

HCID 59394508HCID 59394508、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 3-(2,5-dimethyl-pyrrol-1-yl)-1-methyl-1H-pyrazole (1.5 g, 8.6 mmol) in THF (100 mL) at −78° C., 2.5M nBuLi in Hexane (4.1 mL, 10.3 mmol) is added and stirred for 1.5 hours followed by the addition of trifluoro-acetic acid ethyl ester (1.5 g, 10.3 mmol). After 10 min the ice bath is removed and the reaction is allowed to reach room temperature. Then the reaction is cooled down to −78° C. again and methylmagnesium bromide (1.0 M solution in hexane, 8.6 mL) is added. After 5 min the ice bath is removed and the mixture is stirred at room temperature for 3 hour, poured into water, separated, and the water layer is extracted with DCM. The organic layers are combined and concentrated. The residue is purified by FCC to give the title compound. MS (ESI) m/z 288.1 (M+1).

後処理

  1. customAfter 10 min the ice bath is removed
  2. customto reach room temperature
  3. additionmethylmagnesium bromide (1.0 M solution in hexane, 8.6 mL) is added
  4. customAfter 5 min the ice bath is removed
  5. stirringthe mixture is stirred at room temperature for 3 hour
  6. additionpoured into water
  7. customseparated
  8. extractionthe water layer is extracted with DCM
  9. concentrationconcentrated
  10. customThe residue is purified by FCC

出典と根拠

ORDレコード
ord-481c7e95d52345e5a01614e6bb39f2fd
出典データセット
uspto-grants-2013_09
特許番号
US08541432B2

反応ノート

読み込み中…