Diethyl Ether → Ethyl-12-(m-nitrophenyl)-11-dodecenoate

HRID 2106980Notes

Reaction equation

HRID 2106980 reaction equation
[NH2-].[Na+].[Br-].[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:6][CH2:7][CH3:8])=[O:5].[N+:39]([C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[CH:45]=O)([O-:41])=[O:40].CCOCC>O1CCCC1.O>[CH2:7]([O:6][C:4](=[O:5])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH:45][C:44]1[CH:47]=[CH:48][CH:49]=[C:42]([N+:39]([O-:41])=[O:40])[CH:43]=1)[CH3:8]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 74493-NitrobenzaldehydeHCID 24533Sodium amideHCID 1906338411-Carbethoxyundecyltriphenylphosphonium bromide

Product 1

HCID 53714556Ethyl-12-(m-nitrophenyl)-11-dodecenoateYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

Sodium amide (0.40 g, 9.74 mmol) was weighed directly into a flame-dried 50 ml round-bottomed flask filled with Argon. 11-Carbethoxyundecyltriphenylphosphonium bromide (5.00 g, 9.0 mmol was added. The mixture was cooled to -30° C. After the reaction mixture had stirred for 30 minutes at -30° C., a solution of m-nitrobenzaldehyde (1.4 g, 9.30 mmol) in anhydrous tetrahydrofuran (THF, 2 ml) was added drop-wise. The reaction mixture was allowed to warm to room temperature and was stirred for 4 hours. Ether was added. The reaction mixture was cooled to 0° C. and H2O was cautiously added to destroy residual base. The ether layer was removed, washed with H2O, 2% NaHSO4 and brine, and dried (MgSO4). The solvent was evaporated under reduced pressure to yield an oily residue. Purification by column chromatography (150 g silica gel, hexane:ethyl acetate, 15:1) gave the pure compound 4, ethyl-12-(m-nitrophenyl)-11-dodecenoate (1.323 g, 42% yield).

Workup

  1. additionfilled with Argon
  2. temperatureto warm to room temperature
  3. stirringwas stirred for 4 hours
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. customto destroy residual base
  6. customThe ether layer was removed
  7. washwashed with H2O, 2% NaHSO4 and brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated under reduced pressure
  10. customto yield an oily residue
  11. customPurification by column chromatography (150 g silica gel, hexane:ethyl acetate, 15:1)

Sources & evidence

ORD record
ord-7d96abed146a45e5a1ccc340aa8af9fe
Source dataset
uspto-grants-1990_06
Patent number
US04933157

Reaction notes

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