Tetrahydrofuran → HCID 20313245, compound

HRID 2420177Notes

Reaction equation

HRID 2420177 reaction equation
[OH:1][C:2]([O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][CH2:24][CH2:23]2)([CH:9]1[O:14][CH2:13][C:12](=O)[N:11]([CH:16]([CH3:18])[CH3:17])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[OH:1][C:2]([O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][CH2:24][CH2:23]2)([CH:9]1[O:14][CH2:13][CH2:12][N:11]([CH:16]([CH3:18])[CH3:17])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70624585HCID 70624585, compound

Product 1

HCID 20313245HCID 20313245, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

After mixing 2.5 g. of 2-(1-hydroxy-1-phenyl-5-indanyloxymethyl)-4 -isopropyl-5-oxomorpholine, 100 ml. of tetrahydrofuran, and 1.0 g. of lithium aluminum hydride under ice-cooling, the mixture was stirred for 18 hours at room temperature and then 1 ml. of water, 1 ml. of aqueous 15% sodium hydroxide aqueous solution, and then 3 ml. of water were added to the mixture followed by stirring for 30 minutes. The mixture thus obtained was filtered and the filtrate was distilled and the residue formed was adsorbed on a silica gel column prepared from 50 ml. of silica gel in chloroform and eluted with ethyl acetate. After removing the first 5 ml. of the ethyl acetate eluate, 200 ml. of the subsequent ethyl acetate eluate was collected and dried to provide 2.05 g. (yield 85.3%) of 2-(1-hydroxy-1-phenyl-5-indanyloxymethyl)-4-isopropylmorpholine.

Workup

  1. additionAfter mixing 2.5 g
  2. stirringby stirring for 30 minutes
  3. customThe mixture thus obtained
  4. filtrationwas filtered
  5. distillationthe filtrate was distilled
  6. customthe residue formed
  7. customprepared from 50 ml
  8. washof silica gel in chloroform and eluted with ethyl acetate
  9. customAfter removing the first 5 ml
  10. customof the subsequent ethyl acetate eluate was collected
  11. customdried
  12. customto provide 2.05 g

Sources & evidence

ORD record
ord-20361a89965341479f430fc468a82e6a
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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