Hydrochloric Acid → HCID 11278070, Verbindung

HRID 854992

Reaktionsgleichung

Reaktionsgleichung von HRID 854992
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18]CC)=[O:17])=[CH:7]2.[CH2:22]1COC[CH2:23]1.CO.O[Li].O.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:22]#[CH:23])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([OH:18])=[O:17])=[CH:7]2

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 58934641ethyl 8-chloro-6-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Produkt 1

HCID 11278070HCID 11278070, VerbindungAusbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To 450 mg (1.36 mmole) of ethyl 8-chloro-6-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate was added 9 mL of a solvent mixture of THF/MeOH (7:2) followed by 172 mgs of LiOH—H2O in 1 mL of H2O. The mixture was stirred for 30 min at rt. The mixture was concd, treated with 10 mL of water and acidified with conc. HCl (approx. 0.4 mL). The producted oiled out of solution and was extracted three times with diethyl ether. Combined extracts were dried and concd to afford 0.32 g of a crude yellow solid. Chromatography (C18, Gilson 10×4 cm, 7 injections of 50 mgs each) afforded 0.18 g (43.7%) of a white solid: 1H NMR (d6-acetone/400 MHz) 3.74 (s, 1H), 6.03 (q, 1H, 6.8 Hz), 7.61 (m, 2H), 7.92 (s, 1H); 13C NMR (d6-acetone/400 MHz) 72.0 (q, J=33.2 Hz), 80.0, 81.6, 118.3, 119.6, 121.7, 121.8 (q, J=0.7 Hz), 124.2 (q, J=286.6 Hz), 132.5, 136.1, 136.7, 149.9, 164.6; 19F NMR (d6-acetone/400 MHz) −79.6 (d, 3F, J=6.5 Hz); MS (ES+) 303 (M+1, 27), 291 (65), 289 (51), 235 (100), 233 (79); MS(ES−) 301 (M−1, 100), 303 (35); HRMS (EI−) m/z calcd for (C13H5O3ClF3) 300.9874, found 300.9837.

Aufarbeitung

  1. extractionwas extracted three times with diethyl ether
  2. customCombined extracts were dried
  3. customto afford 0.32 g of a crude yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-298815e0135747f4a58bfa6ca9133168
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

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