Hexane → HCID 131727569, compound

HRID 2100590Notes

Reaction equation

HRID 2100590 reaction equation
CCCCCC.[H-].[Na+].[CH3:9][O:10][C:11]([CH2:13]P(OC)(OC)=O)=[O:12].[Cl:20][C:21]1[CH:31]=[C:30]([CH2:32][CH2:33][CH3:34])[CH:29]=[C:28]([CH:35]=O)[C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1COCC1>[Cl:20][C:21]1[CH:31]=[C:30]([CH2:32][CH2:33][CH3:34])[CH:29]=[C:28](/[CH:35]=[CH:13]/[C:11]([O:10][CH3:9])=[O:12])[C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 86090107Ethyl 2-chloro-6-formyl-4-propylbenzoate

Product 1

HCID 131727569HCID 131727569, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of hexane-washed sodium hydride (0.14 g of 60% suspension in mineral oil, 3.45 mmol) in 20 mL of THF was added trimethyl phosphonoacetate (0.56 mL, 3.45 mmol). The resulting mixture was stirred for 30 min at ambient temperature, at which time a white slurry was obtained. To this slurry was added ethyl 2-chloro-6-formyl-4-propylbenzoate (0.80 g, 3.14 mmol) dropwise in 5 mL of THF. The resulting solution was stirred at ambient temperature for 1 h, at which time the mixture had become homogeneous. The reaction mixture was quenched with water and extracted with ethyl acetate. The organics were washed sequentially with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 0.92 g (95%) of the title compound which was sufficiently pure to be used without purification. 1H NMR (CDCl3): δ 7.58 (d, 1H, J=15.9 Hz), 7.25 (s, 1H), 7.18 (s, 1H), 6.33 (d, 1H, J=15.9 Hz), 4.40 (q, 2H, J=7.2 Hz), 3.73 (s, 3H), 2.52 (t, 2H, J=7.5 Hz), 1.60-1.52 (m, 2H), 1.35 (t, 3H, J=7.1 Hz), 0.88 (t, 3H, J=7.4 Hz). LRMS (ESI): 333.1 (M+H+Na)+.

Workup

  1. customwas obtained
  2. stirringThe resulting solution was stirred at ambient temperature for 1 h, at which time the mixture
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organics were washed sequentially with 1N HCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through a pad of silica gel
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d15877371685433f9b20c5af4f144880
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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