Potassium Carbonate → HCID 23072362, compound

HRID 1182514Notes

Reaction equation

HRID 1182514 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[SH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:5]=1[C:3]([CH2:2][S:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 691792-Bromo-2'-acetonaphthoneHCID 109096145-sulfanylpentanoic Acid

Product 1

HCID 23072362HCID 23072362, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bromomethyl-2-naphthyl ketone (2 g, 8.00 mmol) in anhydrous THF (50 mL) was added 5-mercaptovaleric acid (1.07 g, 8.00 mmol), followed by potassium carbonate (5.71 g, 41 mmol). The suspension was refluxed for 1 hour, cooled to the room temperature and filtered. The solid was collected, dissolved in a 1:1 mixture water-THF and acidified with HCl (pH 1-2). The acidic solution was extracted with ether, dried (MgSO4), filtered and evaporated to produce the title compound 225a (1.21 g, 50% yield). 1H NMR: (300 MHz, DMSO-d6) δ 11.98 (br s, 1H), 8.69 (s, 1H), 8.10 (d, J=7.5 Hz, 1H), 8.00-7.98 (m, 3H), 7.67-7.61 (m, 2H), 4.09 (s, 2H), 2.52 (t, J=6.6 Hz, 2H), 2.19 (t, J=6.6 Hz, 2H), 1.56-1.53 (m, 4H).

Workup

  1. temperatureThe suspension was refluxed for 1 hour
  2. filtrationfiltered
  3. customThe solid was collected
  4. dissolutiondissolved in a 1:1 mixture water-THF
  5. extractionThe acidic solution was extracted with ether
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e23eb8c129c54e7793629c40126966cf
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

Loading…