Ethyl Acetate → HCID 54122061, compound

HRID 2210088Notes

Reaction equation

HRID 2210088 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:14]=[CH:13][C:7]2[C:8](=[O:12])[CH:9]=[CH:10][O:11][C:6]=2[C:5]=1[CH2:15][CH:16]=[CH2:17].[CH3:18][O:19][C:20](=[O:44])[CH2:21][CH2:22][C:23]1[C:28]([O:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]I.C(OCC)(=O)C>CN(C)C=O>[CH3:18][O:19][C:20](=[O:44])[CH2:21][CH2:22][C:23]1[C:24]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][O:3][C:4]2[CH:14]=[CH:13][C:7]3[C:8](=[O:12])[CH:9]=[CH:10][O:11][C:6]=3[C:5]=2[CH2:15][CH:16]=[CH2:17])=[CH:25][CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 12693798HCID 12693798, compoundHCID 152965542-(6-Iodohexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl ester

Product 1

HCID 54122061HCID 54122061, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a slurry of 202 mg(5.05 mmol) of 60% sodium hydride-mineral oil dispersion (pre-washed with penlane) in 3 mL of anhydrous N,N-dimethylformamide was added a solution of 0.77 g (3.81 mmol) of 7-hydroxy-8-(2-propenyl)-4H-1-benzopyran-4-one in 12 mL of anhydrous N,N-dimethylformamide, over a 1 min period. The mixture was stirred at room temperature for 15 min whereupon a solution of 2.1 g (4.29 mmol) of 2-(6-iodohexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl ester (example 17) in 15 mL of anhydrous N,N-dimethylformamide was added over a 1 min period. The resulting mixture was stirred at room temperature for 3 hr before being treated with ice-water, and worked-up with ethyl acetate in the usual manner. The oily product was chromatographed on silica gel, eluting with hexane-ethyl acetate mixtures. There was obtained 1.7 g (79.1%) of the title compound as a yellow oil.

Workup

  1. additionwas added over a 1 min period
  2. customThe oily product was chromatographed on silica gel
  3. washeluting with hexane-ethyl acetate mixtures

Sources & evidence

ORD record
ord-301c42ab357645abaa08caf699daee83
Source dataset
uspto-grants-1995_10
Patent number
US05457124

Reaction notes

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