Diethyl Malonate → HCID 13688474, compound

HRID 255996Notes

Reaction equation

HRID 255996 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:19][CH:18]=1>C(O)C>[CH:23](/[C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH2:14][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[CH:22][CH:21]=1)=[CH:24]/[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 13688472HCID 13688472, compound

Product 1

HCID 13688474HCID 13688474, compoundYield 125.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium (0.408 g, 17.7 mmol) in ethanol (50 ml) under nitrogen was treated with diethyl malonate, (2.84 g, 17.7 mmol) followed by 1-bromo-2-(4-[(Z)1-undecenyl]phenoxy)ethane, (1.30 g, 3.68 mmol). The solution was refluxed 30 h, then cooled and evaporated in vacuo to dryness. The residue was partitioned between ethyl acetate and water and the organic phase separated, washed with water, and dried, (MgSO4). Evaporation in vacuo gave 2.0 g of a yellow oil which was purified by column chromatography using silica gel, eluting with dichloromethane: n-hexane, [2:3] to yield 510 mg (32%) of the title compound as a colourless oil. νmax (film) 1510, 1570 (weak) 1608, 1735, 1753 cm-1 δ(CDCl3) 0.84 (3H, distorted t, terminal CH3), 1.25 (3H, t, J 7 Hz ester CH3), 1.25 (14H, m, (CH2 )7), 2.31 (4H, m, OCH2CH2, allylic CH2), 3.63 (1H, t, J 7 Hz, CH(CO2Et)2), 4.01 (2H, t, J 7 Hz, OCH2), 4.18 (4H, q, J 7 Hz, ester CH2), 5.54 (1H, d.t, Jd 12 Hz, Jt 7 Hz, =CH--alkyl), 6.31 (1H, d, J 12 Hz, ArCH=), 7.02 (4H, ABq, Δν 34 Hz, J 9 Hz, C6H4).

Workup

  1. temperatureThe solution was refluxed 30 h
  2. temperaturecooled
  3. customevaporated in vacuo to dryness
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe organic phase separated
  6. washwashed with water
  7. customdried
  8. customEvaporation in vacuo

Sources & evidence

ORD record
ord-d7110a0c69aa47279760996daaec9b86
Source dataset
uspto-grants-1987_10
Patent number
US04699995

Reaction notes

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