Tetrahydrofuran → HCID 20313234, compound

HRID 2420172Notes

Reaction equation

HRID 2420172 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][CH:23]2[CH3:29])([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][CH:23]2[CH3:29])([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 20313238HCID 20313238, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20313234HCID 20313234, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

After mixing 2.5 g. of 2-(1-hydroxy-3-methyl-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 15% sodium hydroxide aqueous solution, and then 3 ml. of water were added to the mixture followed by stirring for 30 minutes. The mixture was then filtered and the filtrate recovered was dried under reduced pressure. The residue formed was adsorbed on a silica gel column prepared from 50 ml. of silica gel in chloroform and then eluted using ethyl acetate as the eluent. After removing the first 5 ml. of the ethyl acetate eluate emerging from the column, 150 ml. of the subsequent ethyl acetate eluate was collected and dried to provide 2.0 g. (yield 83.0%) of 2-(1-hydroxy-3-methyl-1-phenyl-5-indanyloxymethyl)-4-isopropylmorpholine.

Workup

  1. additionAfter mixing 2.5 g
  2. stirringby stirring for 30 minutes
  3. filtrationThe mixture was then filtered
  4. customthe filtrate recovered
  5. customwas dried under reduced pressure
  6. customThe residue formed
  7. customprepared from 50 ml
  8. washof silica gel in chloroform and then eluted
  9. customAfter removing the first 5 ml
  10. customof the subsequent ethyl acetate eluate was collected
  11. customdried
  12. customto provide 2.0 g

Sources & evidence

ORD record
ord-c00dd0d1a8b54a9d8b5bdcfc5dbd6bc4
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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