Sodium Iodide → HCID 54385391, compound

HRID 1648074Notes

Reaction equation

HRID 1648074 reaction equation
[CH3:1][O:2][C:3](=[O:35])[CH2:4][CH2:5][C:6]1[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]S(C)(=O)=O)=[CH:10][CH:9]=[CH:8][C:7]=1[O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32].O[C:37]1[CH:47]=[CH:46][C:40]2[C:41](=[O:45])[CH2:42][CH2:43][O:44][C:39]=2[C:38]=1[CH2:48][CH2:49][CH3:50].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CCOCC.C(#N)C>[CH3:1][O:2][C:3](=[O:35])[CH2:4][CH2:5][C:6]1[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:37]2[CH:47]=[CH:46][C:40]3[C:41](=[O:45])[CH2:42][CH2:43][O:44][C:39]=3[C:38]=2[CH2:48][CH2:49][CH3:50])=[CH:10][CH:9]=[CH:8][C:7]=1[O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 53661145HCID 53661145, compound

Product 1

HCID 54385391HCID 54385391, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.68 g (1.3 mmol) of 2-[(8-methoxy-8-oxooctyl)oxy]-6-[6-[(methylsulfonyl)oxy]hexyl]benzenepropanoic acid methyl ester from the preceding example, 0.24 g (1.17 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, 0.26 g (1.88 mmol) of anhydrous granular potassium carbonate, 0.215 g (1.43 mmol) of anhydrous sodium iodide, and 10 mL of dry acetonitrile was stirred and refluxed for 24 hr. After being cooled, the reaction mixture was poured onto ice-water and worked-up with ether in the usual manner. The crude product was flash-chromatographed on silica gel, eluting with 2:1 hexane-ethyl acetate. There was obtained 0.69 g (94.5%) of 2-[(8-methoxy-8-oxooctyl)oxy]-6-[6-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)-oxy]hexyl]benzenepropanoic acid methyl ester as a colorless oil. A solution of this diester and 2.5 mL of 3N aqueous lithium hydroxide in 15 mL of tetrahydrofuran was stirred at room temperature for 24 hr. The solvent was removed under reduced pressure and the residue was dissolved in water. The resulting solution was extracted with ether (the extracts were discarded) and then acidified with 3N aqueous hydrochloric acid. Work-up with ether in the usual manner gave an oily acid product which was flash-chromatographed on silica gel, eluting with 90:10:1 chloroform-methanol-acetic acid. Recrystallization of the pure acid from hexane-ethyl acetate afforded 0.5 g (76%) of the title compound as a colorless solid, mp 79°-81° C.

Workup

  1. temperaturerefluxed for 24 hr
  2. temperatureAfter being cooled
  3. additionthe reaction mixture was poured onto ice-water
  4. customThe crude product was flash-chromatographed on silica gel
  5. washeluting with 2:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-30052949a4564e02bf7ec0bdb04e0ea5
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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