Tetrahydrofuran → HCID 20313243, compound

After adding dropwise a solution of 5 g. of methyl magnesium bromide in 27 ml. of tetrahydrofuran to a mixture of 4.0 g. of 4-isopropyl-5-oxo-2-(1-oxo-5-indanyloxymethyl)morpholine and 100 ml. of tetrahydrofuran with stirring at room temperature, the mixture was stirred for 3 hours at room temperature. Then, after adding a small amount of water to the reaction mixture, the solvent was distilled off under reduced pressure. To the residue formed were added 50 ml. of ethyl acetate and 50 ml. of water to dissolve the residue and they were filtered. The ethyl acetate filtrate (100 ml.) was recovered, washed twice each with 50 ml. of saturated sodium chloride aqueous solution, and condensed under reduced pressure, the obtained residue was adsorbed on a silica gel column prepared from 100 ml. of silica gel in chloroform, and then eluted using ethyl acetate as the eluting solution. After removing the first 30 ml. of the ethyl acetate eluting solution emerging from the column, 300 ml. of the subsequent ethyl acetate eluting solution was collected and dried to provide 2.5 g. (yield 59.3%) of oily 2-(1-hydroxy-1-methyl-5-indanyloxymethyl)-4-isopropyl-5-oxomorpholine.

1. additionAfter adding dropwise a solution of 5 g
2. distillationthe solvent was distilled off under reduced pressure
3. customTo the residue formed
4. additionwere added 50 ml
5. filtrationwere filtered
6. customThe ethyl acetate filtrate (100 ml.) was recovered
7. washwashed twice each with 50 ml
8. customof saturated sodium chloride aqueous solution, and condensed under reduced pressure
9. customprepared from 100 ml
10. washof silica gel in chloroform, and then eluted
11. customAfter removing the first 30 ml
12. customof the subsequent ethyl acetate eluting solution was collected
13. customdried
14. customto provide 2.5 g

ORD record

ord-307963a13ca641af9e8b3f89dd75c8cf

Source dataset

uspto-grants-1978_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04109088