Sodium Iodide → HCID 15078340, compound

HRID 2231895Notes

Reaction equation

HRID 2231895 reaction equation
[H-].[Na+].C([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1([CH3:23])[CH:14](CCC)[CH2:13][C:12]2[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:11]=2[O:10]1)C.Br[CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:38])[CH3:37])=[C:32]([OH:39])[C:31]=1[CH2:40][CH2:41][CH3:42].[I-].[Na+].[CH3:45][CH2:46][CH2:47]CCC>CN(C)C=O>[C:36]([C:33]1[CH:34]=[CH:35][C:30]([O:29][CH2:28][CH2:27][CH2:26][O:22][C:20]2[CH:19]=[CH:18][C:12]3[CH2:13][CH2:14][C:9]([CH3:23])([CH2:8][CH2:7][C:6]([OH:5])=[O:24])[O:10][C:11]=3[C:21]=2[CH2:45][CH2:46][CH3:47])=[C:31]([CH2:40][CH2:41][CH3:42])[C:32]=1[OH:39])(=[O:38])[CH3:37]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 8058HexaneHCID 24758Sodium hydrideHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 53813099HCID 53813099, compound

Product 1

HCID 15078340HCID 15078340, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred slurry of 108 mg of 50% sodium hydride-mineral oil dispersion (prewashed with hexane) in 1 ml of anhydrous N,N-dimethylformamide was added a solution of 268 mg of racemic-3,4-dihydro-7-hydroxy-2-methyl-3-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester in 3 ml of dry N,N-dimethylformamide at room temperature, over a 1 minute period. After being stirred for 30 minutes at room temperature, the mixture was treated dropwise with a solution of 313 mg of 4'-(3-bromopropoxy)-2'-hydroxy-3'-n-propylacetophenone in 3 ml of dry N,N-dimethylformamide. Sodium iodide (0.3 g) was added and the mixture was stirred at room temperature for 2.5 hours before being quenched with 1 ml of water. After 30 minutes, 0.3 g of lithium hydroxide monohydrate and 1 ml of water were added and stirring was continued for 3 hours. The mixture was acidified to pH 1 with 1N hydrochloric acid and worked-up with ether in the usual manner. The orange oily product (0.7 g) was chromatographed on 50 g of silica gel. Elution with 4:1 toluene-ethyl acetate gave 310 mg (69.1%) of racemic-7-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3,4-dihydro-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid as a viscous yellow oil after drying at 60° C. under high vacuum.

Workup

  1. stirringthe mixture was stirred at room temperature for 2.5 hours
  2. custombefore being quenched with 1 ml of water
  3. waitAfter 30 minutes
  4. addition0.3 g of lithium hydroxide monohydrate and 1 ml of water were added
  5. stirringstirring
  6. waitwas continued for 3 hours
  7. customThe orange oily product (0.7 g) was chromatographed on 50 g of silica gel
  8. washElution with 4:1 toluene-ethyl acetate

Sources & evidence

ORD record
ord-997d451731be4ccb9605368aef74dd47
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

Loading…