Diethyl Ether → HCID 21866641, compound

HRID 1794264Notes

Reaction equation

HRID 1794264 reaction equation
CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[N:27]=[C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:29][C:30]=1[CH3:31])([CH3:18])[C:14](OC)=[O:15].[OH-].[Na+]>O.O1CCCC1>[CH3:18][C:13]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[N:27]=[C:28]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:29][C:30]=1[CH3:31])([CH3:12])[CH2:14][OH:15]

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21866642HCID 21866642, compound

Product 1

HCID 21866641HCID 21866641, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 214 ml of dry ether, 1.35 g of lithium aluminum hydride was added, and a solution of 10.7 g of methyl 2-methyl-2-[6-(5-methyl-2-phenyloxazol-4-yl)hexyloxy]propionate/40 ml of dry ether was added dropwise with stirring under ice-cooling and stirred for 1 hour. To the mixture was added dropwise 43 ml of tetrahydrofuran/1.7 ml of water followed by addition of 6.3 ml of water and 1.7 ml of 1 N sodium hydroxide, and the mixture was stirred for 15 minutes and filtrated to remove insolubles. The filtrate was concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=3:1) to provide 8.44 g of the objective compound.

Workup

  1. temperaturecooling
  2. stirringstirred for 1 hour
  3. stirringthe mixture was stirred for 15 minutes
  4. filtrationfiltrated
  5. customto remove insolubles
  6. concentrationThe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f060b8316b5c4aa289543f8d9eb50e4f
Source dataset
uspto-grants-2006_04
Patent number
US07022723B2

Reaction notes

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