Tetrahydrofuran → 2-(4-Benzylmorpholin-2-yl)ethan-1-ol

HRID 1460203Notes

Reaction equation

HRID 1460203 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]1([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH:21]([CH2:25][C:26](OCC)=[O:27])[CH2:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O>[C:12]1([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH:21]([CH2:25][CH2:26][OH:27])[CH2:20]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 12582571Ethyl (4-benzylmorpholin-2-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 146525912-(4-Benzylmorpholin-2-yl)ethan-1-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a refluxing mixture of 15 parts of lithium aluminum hydride and 534 parts of tetrahydrofuran was added dropwise a solution of 80 parts of ethyl 4-(phenylmethyl)-2-morpholineacetate (described in C.A.; 93, 26362g) in 89 parts of tetrahydrofuran under a nitrogen atmosphere. Refluxing was continued overnight. After cooling to 0°-5° C., there were added successively 15.6 parts of water, 14.6 parts of NaOH 20% and 51 parts of water. The whole was stirred for 1/2 hour and then filtered over diatomaceous earth. The filtrate was evaporated, yielding 68 parts (99.1%) of 4-(phenylmethyl)-2-morpholineethanol (interm. 4).

Workup

  1. temperatureRefluxing
  2. temperatureAfter cooling to 0°-5° C.
  3. filtrationfiltered over diatomaceous earth
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-3ed74f0ca6a94d2ab5f3824ad6ae80bc
Source dataset
uspto-grants-1991_12
Patent number
US05070090

Reaction notes

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