Tetrahydrofuran → HCID 20313235, compound

HRID 2420179Notes

Reaction equation

HRID 2420179 reaction equation
[CH:1]([N:4]1[C:9](=O)[CH2:8][O:7][CH:6]([C:11]([O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[CH2:19][CH2:18][CH2:17]3)=[O:12])[CH2:5]1)([CH3:3])[CH3:2].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[OH:12][CH:11]([O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[CH2:19][CH2:18][CH2:17]2)[CH:6]1[O:7][CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70624490HCID 70624490, compound

Product 1

HCID 20313235HCID 20313235, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

After mixing 3.03 g, of 4-isopropyl-5-oxo-2-(1-oxo-5-indanyloxymethyl)morpholine, 100 ml. of tetrahydrofuran, and 2.0 g. of lithium aluminum hydride under ice-cooling, the mixture was stirred for 18 hours at room temperature. Then, 2.0 ml. of water, 2.0 ml. of 15% sodium hydroxide aqueous solution, and then 6 ml. of water were added to the mixture followed by stirring for 30 minutes. The mixture was then filtered and the filtrate was concentrated. The residue formed was adsorbed on a silica gel column prepared from 100 ml. of silica gel in chloroform and then eluted with ethyl acetate as the eluent. After removing the first 20 ml. of the ethyl acetate eluate emerging from the column, 300 ml. of the subsequent ethyl acetate eluate was collected and dried to provide 2.0 g. (yield 68.7%) of oily 2-(1-hydroxy-5-indanyloxymethyl)-4-isopropylmorpholine.

Workup

  1. additionAfter mixing 3.03 g
  2. stirringby stirring for 30 minutes
  3. filtrationThe mixture was then filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue formed
  6. customprepared from 100 ml
  7. washof silica gel in chloroform and then eluted with ethyl acetate as the eluent
  8. customAfter removing the first 20 ml
  9. customof the subsequent ethyl acetate eluate was collected
  10. customdried
  11. customto provide 2.0 g

Sources & evidence

ORD record
ord-f14b0f891606450fb71157fb269ff1af
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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