Triethyl phosphonoacetate → HCID 67409342, Verbindung

HRID 1526415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526415
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.CC(C)([O-])C.[K+].[CH2:21]([O:28][C:29]1[CH:37]=[CH:36][C:35]2[N:34]3[CH2:38][CH2:39][C:40](=O)[C:33]3=[CH:32][C:31]=2[CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([O:28][C:29]1[CH:37]=[CH:36][C:35]2[N:34]3[CH2:38][CH2:39]/[C:40](=[CH:9]\[C:10]([O:12][CH2:13][CH3:14])=[O:11])/[C:33]3=[CH:32][C:31]=2[CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 13345Triethyl phosphonoacetateHCID 216859796-Phenylmethoxy-1,2-dihydropyrrolo[1,2-a]indol-3-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 67409342HCID 67409342, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a 5000 mL 3-neck round bottom flask at room temperature under N2 equipped with a mechanical stirrer, an addition funnel, and a temperature probe containing a solution of ethyl 2-(diethoxyphosphoryl)acetate (114 mL, 577 mmol) in THF (2.0 L) was added potassium t-butoxide (1.0 M in THF, 554 mL, 554 mmol) via addition funnel over 10 minutes (temp increase from 22° C. to 29° C.). The reaction mixture was stirred for 2 h and 7-(benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one (123 g, 444 mmol) was added in 4 portions. An additional amount of THF (750 mL) was added to further dissolve ketone. The mixture was stirred at room temperature for 16 h. Anaylasis of an aliquat from the reaction mixture using LC/MS revealed approximately 75-85% conversion to the title compound.

Aufarbeitung

  1. customTo a 5000 mL 3-neck round bottom flask at room temperature under N2 equipped with a mechanical stirrer, an addition funnel
  2. additionvia addition funnel over 10 minutes
  3. temperature(temp increase from 22° C. to 29° C.)
  4. stirringThe mixture was stirred at room temperature for 16 h

Quellen und Nachweise

ORD-Eintrag
ord-ba1703ae2c814dcba5af1c6c5eafdb9d
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085581B2

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