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

HRID 2209446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2209446
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]

Komponenten

8

Edukt 5

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

Produkt 1

HCID 53953280Ethyl 5-(1-acetyl-1H-indol-3-yl)pent-2-enoateAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirring solution of oxalyl chloride (11.4 mL, 0.13 mol) in CH2Cl2 (440 mL) at -78° C. was added dry DMSO (12.4 mL, 0.17 mol) dropwise. After 5 minutes, gas evolution ceased and the alcohol 4 (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 5 (14 g) as a white solid.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-560c2f84ec854b00beeda4978113bc62
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05455243

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