Diethyl Ether → HCID 53656980, compound

HRID 1606817Notes

Reaction equation

HRID 1606817 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Na].[C:6]([C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][C:28]=1[OH:29])[O:12][CH2:13][CH:14]([OH:25])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=1)(=[O:8])[CH3:7].[CH3:30][CH2:31][O:32]CC>CS(C)=O.C(OCC)(=O)C(OCC)=O.C(O)C.Cl>[C:2]([C:3]1[O:29][C:28]2[C:9]([C:6](=[O:8])[CH:7]=1)=[CH:10][C:11]([O:12][CH2:13][CH:14]([OH:25])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=1)=[CH:26][CH:27]=2)([O:32][CH2:31][CH3:30])=[O:1]

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 54175761HCID 54175761, compound

Product 1

HCID 53656980HCID 53656980, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent2×HCID 7268Diethyl OxalateSolvent

Procedure

To a suspensioin of sodium ethoxide, prepared from sodium (6.0 g) and ethanol (60 ml) in dry ether (400 ml) and dimethyl sulphoxide (50 ml), was added a suspension of 1-(3-acetyl-4 -hydroxyphenoxy- 2-hydroxy-3-(p-cyanophenoxy) propane (26.2 g) in diethyl oxalate (30 ml). The resulting suspension was heated under reflux for 2 hours, cooled, and poured onto ice (200 g). After acidification with a solution of acetic acid (24 ml) in water (160 ml), the ether layer was separated, and the aqueous layer extracted with ether (3 × 50 ml). The combined organic extracts were evaporated under reduced pressure to give a yellow solid. This was dissolved in ethanol (200 ml) containing hydrochloric acid (20 drops) and the solution heated under reflux for 1 hour. After cooling, the beige solid (20.0 g) was filtered off. Recrystallization from aqueous dioxane gave 1-(2-carbethoxychromon-6-yloxy)-2-hydroxy-3-(p-cyanophenoxy) propane (17.3 g) as pale yellow crystals, m.p. 150°-152° C.

Workup

  1. additionwas added
  2. temperatureThe resulting suspension was heated
  3. temperatureunder reflux for 2 hours
  4. temperaturecooled
  5. additionpoured onto ice (200 g)
  6. customAfter acidification with a solution of acetic acid (24 ml) in water (160 ml), the ether layer was separated
  7. extractionthe aqueous layer extracted with ether (3 × 50 ml)
  8. customThe combined organic extracts were evaporated under reduced pressure
  9. customto give a yellow solid
  10. temperaturethe solution heated
  11. temperatureunder reflux for 1 hour
  12. temperatureAfter cooling
  13. filtrationthe beige solid (20.0 g) was filtered off
  14. customRecrystallization from aqueous dioxane

Sources & evidence

ORD record
ord-915806b50b14411898ebb078df6787ba
Source dataset
uspto-grants-1976_04
Patent number
US03953604

Reaction notes

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