Diethyl Malonate → 2-Nonadecynylpropanedioic acid, diethyl ester

HRID 1885460Notes

Reaction equation

HRID 1885460 reaction equation
Br[CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[H-].[Na+].[C:23]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(O)C>[C:2]([CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:23]([O:31][CH2:32][CH3:33])=[O:30])#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 197643871-Bromo-2-nonadecyne

Product 1

HCID 856665962-Nonadecynylpropanedioic acid, diethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 16.5 g of 1-bromo-2-nonadecyne in 50 ml of ethanol is added to 3.0 g of 60% sodium hydride and 11.4 ml of diethyl malonate in 100 ml of ethanol. This mixture is stirred one hour and then evaporated. The residue is washed with ether, twice with dilute hydrochloric acid and brine. The residue is then purified by flash chromatography, (5% ethyl acetate:petroleum ether), to give 12.1 g of the desired compound as white needles, mp. 33°-34° C.

Workup

  1. customevaporated
  2. washThe residue is washed with ether, twice with dilute hydrochloric acid and brine
  3. customThe residue is then purified by flash chromatography, (5% ethyl acetate:petroleum ether),

Sources & evidence

ORD record
ord-28cb5a1367ce4367b4493c4c4c9e4f50
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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