Dimethyl Sulfoxide → Ethyl 5-(1-acetyl-1H-indol-3-yl)pent-2-enoate

HRID 257742노트

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HRID 257742 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][CH2:24][CH2:25]O)=[CH:15]1)(=[O:13])[CH3:12].CCN(CC)CC.[C:34]([CH:39]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:36][CH2:37][CH3:38])=[O:35]>C(Cl)Cl.CCOCC>[CH2:37]([O:36][C:34](=[O:35])[CH:39]=[CH:25][CH2:24][CH2:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]([C:11](=[O:13])[CH3:12])[CH:15]=1)[CH3:38]

참가 물질

8

반응물 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 19380935HCID 19380935, 화합물

생성물 1

HCID 53953280Ethyl 5-(1-acetyl-1H-indol-3-yl)pent-2-enoate수율 56.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

To a stirring solution of oxalyl chloride (11.4 mL, 0.13 mol) in CH2Cl2 (440 mL) at -78° C. was added dry DMSO (2.4 mL, 0.17 mol) dropwise. After 5 minutes, gas evolution ceased and the alcohol 31 (19 g, 87 mmol) in CH2Cl2 (40 mL) was added. After 30 minutes, NEt3 (73 mL, 0.52 mol) was added to effect a thick slurry. The cooling bath was removed and the reaction stirred for an additional 15 minutes before adding (carbethoxymethylene)triphenyl phosphorane (33.5 g, 96 mmol). After 2.0 hours, the reaction mixture was diluted with ether and then washed with H2O (2 times), 5% KHSO4 and brine, dried (MgSO4), and concentrated. Flash chromatography (20% ethyl acetate/hexanes) gave the olefin 32 (14 g) as a white solid.

후처리

  1. waitAfter 30 minutes
  2. customThe cooling bath was removed
  3. waitAfter 2.0 hours
  4. washwashed with H2O (2 times), 5% KHSO4 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-cd97d7406a17412bbf785e39ad60b9fa
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264420

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