Acetic Acid → Benzyl 4-hydroxy-1H-indole-1-carboxylate

HRID 16569

Reaktionsgleichung

Reaktionsgleichung von HRID 16569
[Si]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 11703628Benzyl 4-(t-butyldimethylsilyloxy)indole-1-carboxylate

Produkt 1

HCID 12622101Benzyl 4-hydroxy-1H-indole-1-carboxylateAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 10 (28.62 g, 75 mmol) in tetrahydrofuran (375 mL) containing acetic acid (4.5 g, 75 mmol) was treated at 0° C. with 1 M tetrabutylammonium fluoride (75 mL, 75 mmol) and the mixture was stirred at 0° C. for 40 min. The solvent was evaporated and the residue was dissolved in diethyl ether (250 mL) and washed with saturated aq. sodium bicarbonate and brine, dried and evaporated to give a brown solid which was washed with cold hexanes to give 11 as white fluffy needles (14.13 g, 70%), mp 118-120° C. (from dichloromethane-hexanes), (lit.11 mp 121-124° C.).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in diethyl ether (250 mL)
  3. washwashed with saturated aq. sodium bicarbonate and brine
  4. customdried
  5. customevaporated
  6. customto give a brown solid which
  7. washwas washed with cold hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7b6517d98c05498aa1c66ec4e8f2faff
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737169B2

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