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

HRID 2303683노트

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HRID 2303683 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

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온도
-70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-81240fd29b0644689b861ae0c90fcb60
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06432981B1

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