Sodium Hydroxide → HCID 15097267, compound

HRID 974701Notes

Reaction equation

HRID 974701 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:19](OCC)=[O:20])[C:14](OCC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[OH:20][CH2:19][CH:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15097258HCID 15097258, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15097267HCID 15097267, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10.29 g of diethyl 2-[5-(2-methoxyethoxy)methoxypentyl]malonate (prepared as described in Preparation 41) dissolved in 100 ml of tetrahydrofuran was added dropwise to 2.40 g of lithium aluminum hydride dispersed in 100 ml of tetrahydrofuran, whilst ice-cooling (at 5° to 7° C.). The mixture was stirred at room temperature for 3 hours, and then 9.60 ml of a 4% w/v aqueous solution of sodium hydroxide was added dropwise at 5° to 9° C. After stirring the mixture for 30 minutes at room temperature, it was filtered with a Celite filter aid, and the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 105 g of silica gel and 6.94 g of the title compound were obtained from the fractions eluted with mixtures of methylene chloride and methanol ranging from 98:2 to 95:5 by volume, as a colorless oil.

Workup

  1. temperaturecooling (at 5° to 7° C.)
  2. stirringAfter stirring the mixture for 30 minutes at room temperature
  3. filtrationit was filtered with a Celite
  4. filtrationfilter aid
  5. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-5822d5048f544d7c862a5a43a14ea4d2
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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