Aluminium lithium hydride → 2-(2-Nonadecynyl)-1,3-propanediol

HRID 248151Notes

Reaction equation

HRID 248151 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH:26]([C:32](OCC)=[O:33])[C:27](OCC)=[O:28])#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CCOCC>[CH2:7]([CH:26]([CH2:27][OH:28])[CH2:32][OH:33])[C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 856665962-Nonadecynylpropanedioic acid, diethyl ester

Product 1

HCID 197643602-(2-Nonadecynyl)-1,3-propanediolYield 56.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 1.8 g of lithium aluminum hydride in 150 ml of ether is prepared at 0° C. To this is added a solution of 11.7 g of 2-nonadecynylpropanedioic acid, diethyl ester in ether. This mixture is refluxed for 4 hours then the reaction is quenched with aqueous sodium sulfate. After stirring for 2 days, the reaction is diluted with ethyl acetate and filtered. The residue is treated with methanol, IN sodium hydroxide and tetrahydrofuran and then evaporated. The residue is dissolved in ether and washed with brine and purified by flash chromatography, (4:6 ethyl acetate:petroleum ether), to give 5.3 g of the desired product as white plates, mp. 55° C.

Workup

  1. customis prepared at 0° C
  2. temperatureThis mixture is refluxed for 4 hours
  3. customthe reaction is quenched with aqueous sodium sulfate
  4. additionthe reaction is diluted with ethyl acetate
  5. filtrationfiltered
  6. additionThe residue is treated with methanol, IN sodium hydroxide
  7. customtetrahydrofuran and then evaporated
  8. dissolutionThe residue is dissolved in ether
  9. washwashed with brine
  10. custompurified by flash chromatography, (4:6 ethyl acetate:petroleum ether),

Sources & evidence

ORD record
ord-1b6b0b85eee5439f9533633fdd429da2
Source dataset
uspto-grants-1993_05
Patent number
US05208223

Reaction notes

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