Water → HCID 70624585, compound

HRID 2420176Notes

Reaction equation

HRID 2420176 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]([N:12]1[C:17](=[O:18])[CH2:16][O:15][CH:14]([C:19]([O:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[CH2:27][CH2:26][CH2:25]3)=[O:20])[CH2:13]1)([CH3:11])[CH3:10].O.C(OCC)(=O)C>O1CCCC1>[OH:20][C:19]([O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][CH2:26][CH2:25]2)([CH:14]1[O:15][CH2:16][C:17](=[O:18])[N:12]([CH:9]([CH3:10])[CH3:11])[CH2:13]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl Acetate2×HCID 70624490HCID 70624490, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 70624585HCID 70624585, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2.7 g. of phenylmagnesium bromide in 20 ml. of tetrahydrofuran was added dropwise to a mixture of 3.03g. of 4-isopropyl-5-oxo-2-(1-oxo-5-indanyloxymethyl)morpholine in 100 ml of tetrahydrofuran with stirring at room temperature and the mixture thus obtained was stirred for 30 minutes. Then, after adding to the mixture a small amount of water, tetrahydrofuran was distilled off under reduced pressure. To the residue formed were added 100 ml. of ethyl acetate and 100 ml. of water to dissolve the residue and the ethyl acetate layer formed was recovered, washed twice each with 50 ml. of water and then 50 ml. of saturated aqueous sodium chloride aqueous solution, and then ethyl acetate was distilled off. The residue formed was adsorbed on a silica gel column prepared from 150 ml. of silica gel in chloroform and then eluted with ethyl acetate. After removing the first 10 ml. of the ethyl acetate eluate emerging from the column, 300 ml. of the subsequent ethyl acetate eluate was collected and dried to provide 2.93 g. (yield 77%) of oily 2-(1-hydroxy-1-phenyl-5-indanyloxymethyl)-4-isopropyl-5-oxomorpholine.

Workup

  1. customthe mixture thus obtained
  2. distillationwas distilled off under reduced pressure
  3. customTo the residue formed
  4. additionwere added 100 ml
  5. customwas recovered
  6. washwashed twice each with 50 ml
  7. distillationof saturated aqueous sodium chloride aqueous solution, and then ethyl acetate was distilled off
  8. customThe residue formed
  9. customprepared from 150 ml
  10. washof silica gel in chloroform and then eluted with ethyl acetate
  11. customAfter removing the first 10 ml
  12. customof the subsequent ethyl acetate eluate was collected
  13. customdried
  14. customto provide 2.93 g

Sources & evidence

ORD record
ord-d7b64752190e414b9239ea0f0a85e83b
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

Loading…