Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate) → HCID 13066475, compound

HRID 1283123Notes

Reaction equation

HRID 1283123 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH2:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12.C1(C)C=CC(S(O[CH2:29][CH2:30][O:31][CH3:32])(=O)=O)=CC=1>[Na].C(O)(C)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH:15]([CH2:29][CH2:30][O:31][CH3:32])[C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:9]=3[O:10][C:2]=12

Participants

5

Reactant 2

HCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)HCID 13066473HCID 13066473, compound

Product 1

HCID 13066475HCID 13066475, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 5360545SodiumSolvent

Conditions

Temperature
40 °C

Procedure

3 g of 5H-[1]benzopyrano[ 2,3-b]pyridin-7-yl-acetone is dissolved in a solution of 0.32 g of metallic sodium in 15 ml of absolute isopropyl alcohol by warming to 50°-60°C. The solution is cooled to 40°C, 3.5 g of 2-methoxyethyl p-toluenesulfonate is added, and the mixture is stirred under reflux for 1.5 hours. The reaction mixture is concentrated, chloroform and water are added to the residue, and the mixture is stirred. The chloroform layer is separated, dried over anhydrous magnesium sulfate and concentrated. The oily residue is column chromatographed over silica gel (100 g) with a mixture of chloroform and ethyl acetate (10:1) as eluent to give 2.0 g of 3-(5H-[1]benzopyrano[ 2,3-b]pyridin-7-yl)-5-methoxy-2-pentanone as a pale yellow transparent oil. nD28 = 1.5764

Workup

  1. temperatureby warming to 50°-60°C
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe reaction mixture is concentrated
  4. additionchloroform and water are added to the residue
  5. stirringthe mixture is stirred
  6. customThe chloroform layer is separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customchromatographed over silica gel (100 g) with a mixture of chloroform and ethyl acetate (10:1) as eluent

Sources & evidence

ORD record
ord-e3d8e7db89e24e9ab4600ae52246cd7a
Source dataset
uspto-grants-1976_08
Patent number
US03974168

Reaction notes

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