Sodium Hydroxide → (1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid

HRID 606354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606354
Br[CH2:2][C@H:3]1[C@@H:13]2[C@H:4]1[C:5](=[O:16])[O:6][C:7]1[C:8]([F:15])=[CH:9][CH:10]=[C:11]([F:14])[C:12]=12.[OH-:17].[Na+]>O>[F:15][C:8]1[C:7]2[O:17][CH2:2][C@H:3]3[C@@H:4]([C:5]([OH:16])=[O:6])[C@H:13]3[C:12]=2[C:11]([F:14])=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67047808(1S,1aR,7bS)-1-(bromomethyl)-4,7-difluoro-1a,7b-dihydrocyclopropa[c]chromene-2(1H)-one

Produkt 1

HCID 21304923(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acidAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(1S,1aR,7bS)-1-(bromomethyl)-4,7-difluoro-1a,7b-dihydrocyclopropa[c]chromen-2(1H)-one (360 mg, 1.2 mmol) was mixed with the solution of NaOH (0.1 g, 2.5 mmol) in 5 ml of water and heated at stirring for 1 h at 90° C. After completion the reaction mixture was cooled down and extracted into diethyl ether (2×20 ml). Water phase was acidified with conc. HCl. The precipitate formed was collected by filtration to give 180 mg of pure product. Mother liquor was extracted into ether and washed with brine, dried over magnesium sulfate. Concentration gave additional 70 mg of product (containing up to 15% of impurities). Overall yield about 92%.

Aufarbeitung

  1. temperatureheated
  2. temperatureAfter completion the reaction mixture was cooled down
  3. extractionextracted into diethyl ether (2×20 ml)
  4. customThe precipitate formed
  5. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a0b6271f83e94565b5ad8b99aeefbd56
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915295B2

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