Diethyl Ether → HCID 21866824, compound

HRID 857197Notes

Reaction equation

HRID 857197 reaction equation
CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19].[OH-].[Na+]>O.O1CCCC1>[Cl:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([CH2:23][OH:24])[CH2:18][OH:19]

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53401795Diethyl (4-chlorobutyl)propanedioate

Product 1

HCID 21866824HCID 21866824, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 214 ml of dry ether was added 8 g of lithium aluminium hydride, and a solution of 26.7 g of diethyl (4-chlorobutyl)malonate/53 ml of dry ether was added dropwise with stirring under ice-cooling. After 1-hour-stirring at room temperature, the mixture was cooled with ice-cold water, and 173 ml of tetrahydrofuran/14.7 ml of water was added gradually. Then, 14.7 ml of 1N sodium hydroxide solution and 35 ml of water were added, stirred for 15 minutes, filtrated to remove insolubles. The filtrate was concentrated to provide 18.2 g of the objective compound as colorless oil.

Workup

  1. temperaturecooling
  2. stirringAfter 1-hour-stirring at room temperature
  3. additionwas added gradually
  4. stirringstirred for 15 minutes
  5. filtrationfiltrated
  6. customto remove insolubles
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-86c1d5687e3c40e7ae5b0e42873ad780
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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