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Sodium Carbonate → 1,1-Dimethylethyl 2-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-1H-pyrrole-1-carboxylate

HRID 1715995
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1715995
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:16]2[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18]([CH3:25])([CH3:24])[CH2:17]2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:26]([N:33]1[CH:37]=[CH:36][CH:35]=[C:34]1B(O)O)([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[OH:15][C:12]1[CH:11]=[CH:10][C:9]([C:8](=[C:16]2[CH2:17][C:18]([CH3:25])([CH3:24])[CH2:19][C:20]([CH3:23])([CH3:22])[CH2:21]2)[C:5]2[CH:4]=[CH:3][C:2]([C:34]3[N:33]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:37]=[CH:36][CH:35]=3)=[CH:7][CH:6]=2)=[CH:14][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 686543984-[(4-Bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Produkt 1

HCID 686545401,1-Dimethylethyl 2-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-1H-pyrrole-1-carboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a round-bottomed flask were added 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (0.127 g, 0.32 mmoL), 1-N—BOC-pyrrole-2-boronic acid (0.21 g, 1.0 mmoL), tetrakis(triphenylphosphine)palladium (0) (0.033 g, 0.029 mmoL), 2 M Na2CO3 (3 mL), and ethylene glycol dimethyl ether (8 mL). The stirred reaction mixture was heated at reflux overnight under a nitrogen atmosphere. The oil bath was removed and the reaction mixture was allowed to cool at RT. The reaction mixture was transferred to a separatory funnel and partitioned between H2O and EtOAc. The organic phase was separated, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to give an orange-brown oil. The crude product was purified by flash chromatography on silica gel with a hexanes:EtOAc gradient (100:0 to 80:20) to give 111 mg (72%) of compound 18 as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 0.88 (s, 12H), 1.24 (m, 11H), 1.92 (s, 2H), 1.94 (s, 2H), 6.19 (m, 1H), 6.23 (m, 1H), 6.65 (d, J=8.5 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 7.09 (d, J=8.1 Hz, 2H), 7.21 (d, J=8.0 Hz, 2H), 7.31 (m, 1H), 9.27 (s, 1H). LCMS (ESI): m/z 508 (M+Na)+.

Aufarbeitung

  1. customThe stirred reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux overnight under a nitrogen atmosphere
  4. customThe oil bath was removed
  5. customThe reaction mixture was transferred to a separatory funnel
  6. custompartitioned between H2O and EtOAc
  7. customThe organic phase was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationthe filtrate was concentrated in vacuo
  11. customto give an orange-brown oil
  12. customThe crude product was purified by flash chromatography on silica gel with a hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6bb261bbc82d4ec196cd3996597ce6cf
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07799828B2

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