Potassium Hydroxide → HCID 57900438, Verbindung

HRID 84686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84686
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([O:17]C)=[O:16])[S:14][C:5]=3[C:4]=2[CH:3]=1.[OH-].[K+]>O1CCCC1.O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([OH:17])=[O:16])[S:14][C:5]=3[C:4]=2[CH:3]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 57900105methyl 8-bromo-4H-thieno[3,2-c]chromene-2-carboxylate

Produkt 1

HCID 57900438HCID 57900438, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a suspension of methyl 8-bromo-4H-thieno[3,2-c]chromene-2-carboxylate 2 (2.64 g, 8.12 mmol, 1 equiv) in 4:1 tetrahydrofuran/water (80 mL) was added aqueous potassium hydroxide (24 mL, 24 mmol, 3.0 equiv, 1.0 M solution in water) at 24° C. After 15 hr, the tetrahydrofuran was removed in vacuo (<20 mm Hg). The resulting aqueous suspension was diluted with water until all the solids were dissolved. To the resulting solution was added concentrated hydrochloric acid until the solution reached pH=1. The resulting solids were collected by filtration and dried in vacuo (<1 mm Hg) to afford 3bp as a yellow solid (2.36 g, 93%). 1H NMR (500 MHz, CDCl3), δ: 13.28 (br s, 1 H), 7.64 (d, J=2.4 Hz, 1 H), 7.60 (s, 1 H), 7.40 (dd, J=8.7, 2.4 Hz, 1 H), 6.94 (d, J=8.7 Hz, 1 H), 5.30 (s, 3 H).

Aufarbeitung

  1. customthe tetrahydrofuran was removed in vacuo (<20 mm Hg)
  2. additionThe resulting aqueous suspension was diluted with water until all the solids
  3. dissolutionwere dissolved
  4. additionTo the resulting solution was added concentrated hydrochloric acid until the solution
  5. filtrationThe resulting solids were collected by filtration
  6. customdried in vacuo (<1 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-4799f09711d34a67b7ba1176b07cd2bd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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