Potassium Carbonate → HCID 67780109, compound

HRID 327971Notes

Reaction equation

HRID 327971 reaction equation
[CH3:1][O:2][C:3](=[O:23])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]S(C)(=O)=O.[O:24]=[C:25]1[CH2:34][CH2:33][CH2:32][C:31]2[C:30](O)=[C:29]([CH2:36][CH:37]=[CH2:38])[CH:28]=[CH:27][C:26]1=2.C(=O)([O-])[O-].[K+].[K+].COCCOCCN(CCOCCOC)CCOCCOC>CCOCC.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:23])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:30]1[C:31]2[CH2:32][CH2:33][CH2:34][C:25](=[O:24])[C:26]=2[CH:27]=[CH:28][C:29]=1[CH2:36][CH:37]=[CH2:38]

Participants

7

Reactant 4

HCID 11430Potassium Carbonate2×HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 199221065-Oxo-2-(2-propenyl)-5,6,7,8-tetrahydro-1-naphthalenolHCID 86747453HCID 86747453, compound

Product 1

HCID 67780109HCID 67780109, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.37 g (4 mmol) of (E)-3-[2-[[5-[(methylsulfonyl)oxy]pentyl]oxy]phenyl]-2-propenoic acid methyl ester from example 76, 0.81 g (4 mmol) of 5-oxo-2-(2-propenyl)-5,6,7,8-tetrahydro-1-naphthalenol, 0.8 g (5.8 mmol) of anhydrous, granular potassium carbonate, 0.08 mL of TDA-1, and 25 mL of toluene was stirred under reflux for 5.5 hr and at room temperature for 12 hr. After being treated with 0.3 g of additional potassium carbonate, the mixture was stirred and refluxed for a further 24 hr. The mixture was cooled and diluted with ether. The organic phase was washed with water and saturated brine and work-up was completed in the usual manner giving a brown oil. This material was chromatographed on 50 g of silica gel. Elution with 1:1 hexane-ether afforded 1.72 g (96%) of (E)-3-[2-[5-[(5-oxo-2-(2-propenyl)-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]pentyloxy]phenyl]-2-propenoic acid methyl ester as a yellow-orange oil.

Workup

  1. stirringthe mixture was stirred
  2. temperaturerefluxed for a further 24 hr
  3. temperatureThe mixture was cooled
  4. washThe organic phase was washed with water and saturated brine
  5. customgiving a brown oil
  6. customThis material was chromatographed on 50 g of silica gel
  7. washElution with 1:1 hexane-ether

Sources & evidence

ORD record
ord-7cef12d55cd345b48b20c32f9bd143d6
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

Loading…