Hydrochloric Acid → HCID 19433777, compound

HRID 1735643Notes

Reaction equation

HRID 1735643 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:32])([F:31])[S:9]([C:12]1[CH:17]=[C:16]([CH2:18][CH2:19][CH2:20][CH2:21]Br)[CH:15]=[C:14]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])[C:13]=1[OH:30])(=[O:11])=[O:10].Cl>C1COCC1>[F:28][C:26]([F:27])([F:29])[S:23]([C:14]1[CH:15]=[C:16]([CH2:18][CH2:19][CH:20]=[CH2:21])[CH:17]=[C:12]([S:9]([C:8]([F:32])([F:31])[F:7])(=[O:11])=[O:10])[C:13]=1[OH:30])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19433775HCID 19433775, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19433777HCID 19433777, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

24.6 g of potassium t-butoxide was dissolved in 200 ml of anhydrous THF under nitrogen. The solution was cooled with a dry ice bath to keep the inside temperature at -30° C. 4.9 g of compound (10) in 20 ml of THF was dropped into the solution and the mixture was stirred for 1 hour followed by warming to the room temperature. Then the reaction mixture was poused into ice, acidified with diluted hydrochloric acid and extracted with ether. After washing, drying and the solvent removal 3.5 g of liquid product was collected. MNR (CDCl3): δ 2.8 (m, 2H), 3.5 (t, 2H), 4.7-5.0 (m, 2H), 5.5-6.2 m, 1H), 7.2 (s, 1H), 8.1 (s, 2H) ppm.

Workup

  1. temperatureThe solution was cooled with a dry ice bath
  2. customat -30° C
  3. extractionextracted with ether
  4. washAfter washing
  5. customdrying
  6. customthe solvent removal 3.5 g of liquid product
  7. customwas collected

Sources & evidence

ORD record
ord-a849d89d8640462386bb17284accb5c7
Source dataset
uspto-grants-1996_07
Patent number
US05538812

Reaction notes

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