Diethyl Ether → HCID 21866910, compound

HRID 1796366Notes

Reaction equation

HRID 1796366 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][C:28](OC)=[O:29].[OH-].[Na+]>O.O1CCCC1>[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][OH:29]

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21866622HCID 21866622, compound

Product 1

HCID 21866910HCID 21866910, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 17 ml of dry ether, 550 mg of lithium aluminum hydride was added and 3.3 g of methyl 5-(5-methyl-2-phenyloxazol-4-yl)-1-pentanoate/10 ml of dry ether was added dropwise. After 1-hour-stirring at room temperature, the mixture was cooled with ice-cold water and 12 ml of tetrahydrofuran/0.7 ml of water was added dropwise gradually. Then, 0.7 ml of 1N sodium hydroxide and 2.5 ml of water were added and stirred for 15 minutes. The mixture was filtrated to remove insolubles and the filtrate was concentrated to provide 2.9 g of the objective compound as yellowish crystals. M.p. 40–42° C.

Workup

  1. additionwas added dropwise gradually
  2. stirringstirred for 15 minutes
  3. filtrationThe mixture was filtrated
  4. customto remove insolubles
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-14554a7a813a44b08a54756e73f08136
Source dataset
uspto-grants-2006_04
Patent number
US07030143B2

Reaction notes

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