Diethyl Ether → HCID 21866748, compound

HRID 1796369Notes

Reaction equation

HRID 1796369 reaction equation
CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][C:13]1[O:17][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:15][C:14]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]([C:35](OCC)=[O:36])[C:30](OCC)=[O:31].[OH-].[Na+]>O.O1CCCC1>[OH:31][CH2:30][CH:29]([CH2:35][OH:36])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:14]1[N:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:17][C:13]=1[CH3:12]

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86595849HCID 86595849, compound

Product 1

HCID 21866748HCID 21866748, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 15 ml of dry ether, 637 mg of lithium aluminium hydride was added, and 2.6 g of diethyl [5-(5-methyl-2-phenyloxazol-4-yl)pentyl]malonate/10 ml of dry ether was added dropwise. After 2-hour-stirring at room temperature, the mixture was cooled with ice-cold water, and 14 ml of tetrahydrofuran/0.8 ml of water was added dropwise gradually. To the mixture were added 0.8 ml of an aqueous solution of 1 N sodium hydroxide and 2.3 ml of water, and stirred for 15 minutes and filtrated to remove insolubles. The filtrate was concentrated to provide 2.0 g of the objective compound as white crystals. M.p. 71–74° C.

Workup

  1. additionwas added dropwise gradually
  2. stirringstirred for 15 minutes
  3. filtrationfiltrated
  4. customto remove insolubles
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f51cdbc471fe4348aa24e167d8d4cf36
Source dataset
uspto-grants-2006_04
Patent number
US07030143B2

Reaction notes

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