Dimethyl Sulfoxide → (+)-trans-3-Formyl-4-phenylcyclopentan-1-one

HRID 2303683ノート

反応式

HRID 2303683 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C@H:13]1[C@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][C:15](=[O:24])[CH2:14]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.O>[CH:12]([C@H:13]1[C@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][C:15](=[O:24])[CH2:14]1)=[O:11]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 53754795(+)-trans-3-Hydroxymethyl-4-phenylcyclopentan-1-one

生成物 1

HCID 54453591(+)-trans-3-Formyl-4-phenylcyclopentan-1-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-70 °C

実験手順

To a solution of oxalyl chloride (0.352 mL, 0.512 g, 4.03 mmol) in methylene chloride (8 mL) at −70° C. was added dropwise DMSO (0.573 mL, 0.630 g, 8.06 mmol). After 10 min, a solution of (+)-trans-3-hydroxymethyl-4-phenylcyclopentan-1-one from Example 11, Step F (0.153 g, 0.807 mmol) in methylene chloride (1 mL) was added dropwise. The reaction mixture was stirred at −70° C. for 45 min and then diisopropylethylamine (2.1 mL, 1.6 g, 4.48 mmol) was added. The reaction mixture was allowed to warm to rt for 10 min and then diluted with methylene chloride, poured into water, and extracted three times with methylene chloride. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude title compound (0.15 g) was used directly in Step B.

後処理

  1. temperatureto warm to rt for 10 min
  2. extractionextracted three times with methylene chloride
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-81240fd29b0644689b861ae0c90fcb60
出典データセット
uspto-grants-2002_08
特許番号
US06432981B1

反応ノート

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