Sodium Iodide → 2-[6-[4-Acetyl-3-hydroxy-2-(3-phenylpropyl)phenoxy]hexyl]-6-[(6-methoxy-6-oxohexyl)oxy]benzenepropanoic acid methyl ester

HRID 1648082Notes

Reaction equation

HRID 1648082 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:6]([OH:17])[CH:5]=[CH:4][C:3]=1[C:18](=[O:20])[CH3:19].[CH3:21][O:22][C:23](=[O:53])[CH2:24][CH2:25][C:26]1[C:31]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]OS(C)(=O)=O)=[CH:30][CH:29]=[CH:28][C:27]=1[O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([O:51][CH3:52])=[O:50].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CCOCC.C(#N)C>[CH3:21][O:22][C:23](=[O:53])[CH2:24][CH2:25][C:26]1[C:27]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([O:51][CH3:52])=[O:50])=[CH:28][CH:29]=[CH:30][C:31]=1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:17][C:6]1[CH:5]=[CH:4][C:3]([C:18](=[O:20])[CH3:19])=[C:2]([OH:1])[C:7]=1[CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 193799221-[2,4-Dihydroxy-3-(3-phenylpropyl)phenyl]ethanoneHCID 542803312-[(6-Methoxy-6-oxohexyl)oxy]-6-[6-(methylsulfonyl)oxyhexyl]benzenepropanoic acid methyl ester

Product 1

HCID 543132862-[6-[4-Acetyl-3-hydroxy-2-(3-phenylpropyl)phenoxy]hexyl]-6-[(6-methoxy-6-oxohexyl)oxy]benzenepropanoic acid methyl esterYield 90.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.81 g (3 mmol) of 1-[2,4-dihydroxy-3-(3-phenylpropyl)phenyl]ethanone from example 191, 1.6 g (3.29 mmol) of 2-[(6-methoxy-6-oxohexyl)oxy]-6-[6-[(methylsulfonyl)oxy]hexyl]benzenepropanoic acid methyl ester from example 156, 0.66 g (4.78 mmol) of anhydrous, granular potassium carbonate, 0.55 g (3.67 mmol) of sodium iodide, and 25 mL of acetonitrile was stirred and refluxed for 18.5 hr. The resulting thick slurry was cooled, diluted with ether, washed with water, 12% aqueous sodium bisulfite, and brine, and work-up was completed in the usual manner. Thin layer chromatographic analysis of the oily product revealed that alkylation was incomplete. Therefore, the product was dissolved in 5 mL of acetonitrile and 0.69 g (5 mmol) of anhydrous, granular potassium carbonate was added. The resulting mixture was stirred and refluxed for 24 hr before being worked-up as described above. The oily product (2.01 g) was chromatographed on 50 g of silica gel. Elution with 1:1 hexane-ether afforded 1.80 g (90.9%) of the title compound as an almost colorless oil.

Workup

  1. temperaturerefluxed for 18.5 hr
  2. temperatureThe resulting thick slurry was cooled
  3. washwashed with water, 12% aqueous sodium bisulfite, and brine
  4. dissolutionTherefore, the product was dissolved in 5 mL of acetonitrile
  5. addition0.69 g (5 mmol) of anhydrous, granular potassium carbonate was added
  6. stirringThe resulting mixture was stirred
  7. temperaturerefluxed for 24 hr
  8. customThe oily product (2.01 g) was chromatographed on 50 g of silica gel
  9. washElution with 1:1 hexane-ether

Sources & evidence

ORD record
ord-dfae3633ddf24b39b07e99d8d50d75e1
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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