Tetrahydrofuran → HCID 20313238, compound

HRID 2420171Notes

Reaction equation

HRID 2420171 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.[CH:14]([N:17]1[C:22](=[O:23])[CH2:21][O:20][CH:19]([C:24]([O:26][C:27]2[CH:28]=[C:29]3[C:33](=[CH:34][CH:35]=2)[CH2:32][CH2:31][CH:30]3[CH3:36])=[O:25])[CH2:18]1)([CH3:16])[CH3:15]>C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[OH:25][C:24]([O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[CH2:32][CH2:31][CH:30]2[CH3:36])([CH:19]1[O:20][CH2:21][C:22](=[O:23])[N:17]([CH:14]([CH3:15])[CH3:16])[CH2:18]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 20313224HCID 20313224, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 20313238HCID 20313238, compoundYield 82.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2.7 g. of phenylmagnesium bromide in 30 ml. of tetrahydrofuran was added dropwise to a mixture of 3.17 g, of 4-isopropyl-2-(3-methyl-1-oxo-5-indanyloxymethyl)-5-oxomorpholine and 200 ml. of tetrahydrofuran with stirring at room temperature and the mixture was further stirred for 30 minutes. Then, adding a small amount of water to the reaction mixture, tetrahydrofuran was distilled off from the reaction mixture under reduced pressure. To the residue formed were added 100 ml. of ethyl acetate and 100 ml. of water to dissolve the residue therein and the ethyl acetate layer formed was recovered and washed twice each with 50 ml. of water and then with 50 ml. of saturated sodium chloride aqueous solution. Then, ethyl acetate was distilled off and the residue formed was adsobed on a silica gel column prepared from 150 ml of silica gel. in chloroform. The residue adsorbed was then eluted with ethyl acetate and after removing the first 10 ml. of the ethyl acetate eluate emerging from the column, 300 ml. of the ethyl acetate eluate thereafter was collected and dried to provide 3.25 g. (yield 82.3%) of oily 2-(1-hydroxy-3-methyl-1-phenyl-5-indanyloxymethyl)-4-isopropyl-5-oxomorpholine.

Workup

  1. distillationwas distilled off from the reaction mixture under reduced pressure
  2. customTo the residue formed
  3. additionwere added 100 ml
  4. customwas recovered
  5. washwashed twice each with 50 ml
  6. distillationThen, ethyl acetate was distilled off
  7. customthe residue formed
  8. customprepared from 150 ml of silica gel
  9. washThe residue adsorbed was then eluted with ethyl acetate
  10. customafter removing the first 10 ml
  11. customof the ethyl acetate eluate thereafter was collected
  12. customdried
  13. customto provide 3.25 g

Sources & evidence

ORD record
ord-cbfea0362b4145b7b8ab23ec742fce3d
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

Loading…