Acetonitrile → HCID 15296556, compound

HRID 2210086Notes

Reaction equation

HRID 2210086 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]I.[OH:28][C:29]1[CH:39]=[CH:38][C:32]2[C:33](=[O:37])[CH2:34][CH2:35][O:36][C:31]=2[C:30]=1[CH2:40][CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CCOCC>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:28][C:29]1[CH:39]=[CH:38][C:32]2[C:33](=[O:37])[CH2:34][CH2:35][O:36][C:31]=2[C:30]=1[CH2:40][CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 152965542-(6-Iodohexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl esterHCID 15296555HCID 15296555, compound

Product 1

HCID 15296556HCID 15296556, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 12.25 g (25 mmol) of 2-(6-iodohexyl)-6-(4-methoxy-4-oxobutoxy)benzenepropanoic acid methyl ester (preceding example), 7.1 g (25.2 mmol) of 2,3-dihydro-7-hydroxy-8-(3-phenylpropyl)-4H-1-benzopyran-4-one (example 9), 8.3 g (60 mmol) of anhydrous potassium carbonate, and 60 mL of dry acetonitrile was stirred and refluxed for 22 hr. After being cooled, the mixture was diluted with ether and filtered with suction. The solids were washed well with ether. The filtrate and washes were combined and concentrated in vacuo giving 16.5 g of a yellow oil. This material was chromatographed on silica gel, eluting with hexane-ethyl acetate mixtures. There was obtained 13.75 g (85.4%) of pure title dimethyl ester, as an oil.

Workup

  1. temperaturerefluxed for 22 hr
  2. temperatureAfter being cooled
  3. filtrationfiltered with suction
  4. washThe solids were washed well with ether
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-526adf34523340f78d3a748efba1b4fe
Source dataset
uspto-grants-1995_10
Patent number
US05457124

Reaction notes

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