Tetrahydrofuran → HCID 20313204, compound

HRID 2420170Notes

Reaction equation

HRID 2420170 reaction equation
O1CCCC1.[CH:6]([N:9]1[C:14](=O)[CH2:13][O:12][CH:11]([C:16]([O:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[CH2:24][CH2:23][CH:22]3[CH3:28])=[O:17])[CH2:10]1)([CH3:8])[CH3:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[OH:17][CH:16]([O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[CH2:24][CH2:23][CH:22]2[CH3:28])[CH:11]1[O:12][CH2:13][CH2:14][N:9]([CH:6]([CH3:8])[CH3:7])[CH2:10]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 20313224HCID 20313224, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20313204HCID 20313204, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In 10 ml. of tetrahydrofuran was dissolved 3.17 g. of 4-isopropyl-2-(3-methyl-1-oxo-5-indanyloxymethyl)-5-oxomorpholine and the solution was added dropwise to the suspension of 0.4 g. of lithium aluminum hydride in 20 ml. of tetrahydrofuran followed by stirring for 5 hours at room temperature. Thereafter, 0.4 ml. of water, 0.4 ml. of aqueous 15% sodium hydroxide solution, and then 1.2 ml. of water were added successively to the mixture followed by stirring for 30 minutes and then the filtrate obtained was concentrated under reduced pressure to provide 2.1 g. (yield 68.8%) of 2-(1-hydroxy-3-methyl-5-indanyloxymethyl)-4-isopropylmorpholine having a boiling point of 174°-178° C./0.5 mm.Hg was obtained.

Workup

  1. stirringby stirring for 30 minutes
  2. customthe filtrate obtained
  3. concentrationwas concentrated under reduced pressure
  4. customto provide 2.1 g

Sources & evidence

ORD record
ord-342869887e394607bf26cec778294573
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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