Cyclohexanecarboxaldehyde → 2-(4-Bromo-2,6-dimethyl-phenyl)-5-(cyclohexyl-hydroxy-methyl)-3-methoxy-cyclopent-2-enone

HRID 1631881ノート

反応式

HRID 1631881 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:16])[CH2:11][CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([CH3:17])[CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:28]1[CH2:33][CH2:32][CH:31]([CH:34]=[O:35])[CH2:30][CH2:29]1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:17])[C:5]([C:9]2[C:10](=[O:16])[CH:11]([CH:34]([CH:31]3[CH2:32][CH2:33][CH2:28][CH2:29][CH2:30]3)[OH:35])[CH2:12][C:13]=2[O:14][CH3:15])=[C:6]([CH3:8])[CH:7]=1

参加物

5

反応物 3

HCID 16275CyclohexanecarboxaldehydeHCID 2733832Lithium HexamethyldisilazideHCID 668681542-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-cyclopent-2-enone

生成物 1

HCID 668685772-(4-Bromo-2,6-dimethyl-phenyl)-5-(cyclohexyl-hydroxy-methyl)-3-methoxy-cyclopent-2-enone

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

To a solution of 2-(4-bromo-2,6-dimethyl-phenyl)-3-methoxy-cyclopent-2-enone (1 g, 3.4 mmol) in 10 ml of dry tetrahydrofuran under nitrogen atmosphere at −78° C. LiHMDS (4.42 ml, 4.42 mmol) is added slowly and it is stirred at −78° C. for 40 minutes. A solution of cyclohexyl carboxaldehyde (761 mg, 6.8 mmol) in dry tetrahydrofuran (10 ml) is added to the reaction mixture at −78° C. The reaction mixture is stirred at this temperature for 2 hours and then at room temperature for 3 hours. The reaction mixture is quenched with water (50 ml) and the aqueous layer is extracted with ethyl acetate (3*100 ml). The combined organic layers are dried with sodium sulfate and concentrated under vacuum to obtain crude product which is directly taken to the next step without further purification.

後処理

  1. customat −78° C
  2. stirringThe reaction mixture is stirred at this temperature for 2 hours
  3. waitat room temperature for 3 hours
  4. customThe reaction mixture is quenched with water (50 ml)
  5. extractionthe aqueous layer is extracted with ethyl acetate (3*100 ml)
  6. dry with materialThe combined organic layers are dried with sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customto obtain crude product which
  9. customis directly taken to the next step without further purification

出典と根拠

ORDレコード
ord-2d4d495a604a4eb4919a799b10d5ca78
出典データセット
uspto-grants-2014_07
特許番号
US08791303B2

反応ノート

読み込み中…