Tetrahydrofuran → 2-{[(1H-Inden-7-yl)oxy]methyl}-4-(propan-2-yl)morpholine

HRID 2420159Notes

Reaction equation

HRID 2420159 reaction equation
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[O:21][CH2:22][CH:23]2[O:28][CH2:27][C:26](=O)[N:25]([CH:30]([CH3:32])[CH3:31])[CH2:24]2)[CH:14]=[CH:13]1.[OH-].[Na+]>C(OCC)(=O)C.O>[CH:30]([N:25]1[CH2:26][CH2:27][O:28][CH:23]([CH2:22][O:21][C:19]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:20]=2[CH2:12][CH:13]=[CH:14]3)[CH2:24]1)([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 12917365HCID 12917365, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 129173702-{[(1H-Inden-7-yl)oxy]methyl}-4-(propan-2-yl)morpholineYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In 50 ml. of anhydrous tetrahydrofuran was suspended 0.5 g. of lithium aluminum hydride and after adding slowly to the suspension a solution of 2.0 g. of 2-(7-indenyloxymethyl)-4-isopropylmorpholin-5-one in 10 ml. of anhydrous tetrahydrofuran with stirring, the mixture was stirred for 10 hours at 40°-50° C. Then, to the reaction mixture thus formed were added 0.5 ml. of water, 0.5 ml. of an aqueous 15% sodium hydroxide solution, and then 1.5 ml. of water successively to decompose excess lithium aluminum hydride. After stirring the mixture for 30 minutes, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue formed was dissolved in a small amount of ethyl acetate and the solution was subjected to a silica gel column chromatography (column diameter 1.5 cm., height 10 cm., eluting solution 200 ml.) to provide 1.5 g. (yield 79%) of oily 4-isopropyl-2-(7-indenyloxymethyl)morpholine.

Workup

  1. customThen, to the reaction mixture thus formed
  2. additionwere added 0.5 ml
  3. stirringAfter stirring the mixture for 30 minutes
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue formed
  7. washthe solution was subjected to a silica gel column chromatography (column diameter 1.5 cm., height 10 cm., eluting solution 200 ml.)
  8. customto provide 1.5 g

Sources & evidence

ORD record
ord-fc43f053c6b240f0a39802555cd8e8ee
Source dataset
uspto-grants-1978_08
Patent number
US04109088

Reaction notes

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