Dimethyl Sulfoxide → 2,3,4,5-Tetrahydro-1-benzoxepin-6-carboxaldehyde

HRID 1602440노트

반응식

HRID 1602440 반응식
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=O.[O:11]1[C:17]2[CH:18]=[CH:19][CH:20]=C[C:16]=2[CH2:15][CH:14](CO)[CH2:13][CH2:12]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]1[C:17]2=[CH:18][CH:19]=[CH:20][C:6]([CH:5]=[O:9])=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12]1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18787485HCID 18787485, 화합물

생성물 1

HCID 187873792,3,4,5-Tetrahydro-1-benzoxepin-6-carboxaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
-78 °C

실험 절차

DMSO (1.85 ml, 26 mmol) was added slowly to a -78° C. solution of oxalyl chloride in methylene chloride (10 ml of 2M, 20 mmol). To this solution was added slowly a solution of 2,3,4,5-tetrahydrobenzoxepin-4-methanol (2.3 g, 13 mmol) in methylene chloride, and the mixture was stirred 30 min at -78° C. Triethyl amine (7.53 ml, 52 mmol) was added slowly to the reaction mixture, which was then allowed to warm to room temperature. The mixture was diluted with methylene chloride (50 ml) and washed with water and then brine. The organic layer was concentrated in vacuo to an oil (2.28 g, 100%).

후처리

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. concentrationThe organic layer was concentrated in vacuo to an oil (2.28 g, 100%)

출처 및 근거

ORD 기록
ord-085348c088d3445ea4123f2fb02aaafc
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05981571

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