Water → ethyl 2-(3,4-dihydronaphthalen-2-yl)acetate

HRID 365489Notes

Reaction equation

HRID 365489 reaction equation
[H-].[Na+].[CH2:3]1[C:12](=O)[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.[OH2:14].[O:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:12]=1[CH2:17][C:16]([O:15][CH2:19][CH3:18])=[O:14]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 682662-Tetralone

Product 1

HCID 313346ethyl 2-(3,4-dihydronaphthalen-2-yl)acetate

Conditions

Temperature
10 °C

Procedure

A solution of 56 g (0.25 mol) of triethyl phosphonoacetate in 70 ml of tetrahydrofuran (THF) is added dropwise to a suspension, maintained at 0° C., of 6 g (0.25 mol) of NaH in 600 ml of anhydrous THF under a nitrogen atmosphere. The mixture is then stirred at 10° C. for 30 minutes, cooled to 0° C., and then treated, dropwise, with a solution of 36.52 g (0.25 mol) of β-tetralone in 50 ml of anhydrous THF. After stirring for 3 hours at 20° C., the mixture is hydrolysed, at 0° C., with 200 ml of water. The solvent is evaporated off under reduced pressure and the residue is extracted with dichloromethane (CH2Cl2)(3×200 ml). The combined organic phases are washed with saturated NaCl solution, dried and concentrated to yield an oily brown residue. Distillation under a partial vacuum allows the title compound to be obtained in the form of a colourless liquid.

Workup

  1. temperaturecooled to 0° C.
  2. additiontreated
  3. stirringAfter stirring for 3 hours at 20° C.
  4. customThe solvent is evaporated off under reduced pressure
  5. extractionthe residue is extracted with dichloromethane (CH2Cl2)(3×200 ml)
  6. washThe combined organic phases are washed with saturated NaCl solution
  7. customdried
  8. concentrationconcentrated
  9. customto yield an oily brown residue
  10. distillationDistillation under a partial vacuum
  11. customto be obtained in the form of a colourless liquid

Sources & evidence

ORD record
ord-3c7194b7bbca4caf8c0d3431ee2c7bd3
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

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