Hydrochloric Acid → Ethyl 3-(2-benzyloxy-ethoxy)-propionate

HRID 551228Notes

Reaction equation

HRID 551228 reaction equation
[CH2:1]([O:8][CH:9](O)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].Cl.C1C[O:24]CC1>>[CH2:1]([O:8][CH2:9][CH2:10][O:24][CH2:15][CH2:14][C:13]([O:17][CH2:18][CH3:19])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8821Ethyl AcrylateHCID 5360545SodiumHCID 19595026Benzyloxyethanol

Product 1

HCID 66731906Ethyl 3-(2-benzyloxy-ethoxy)-propionate

Procedure

8.53 ml (60.0 mmol) benzyloxy-ethanol are combined with 13 mg (0.57 mmol) sodium in 40 ml THF, then when it has dissolved 5.95 ml (54.7 mmol) ethyl acrylate are added under an argon atmosphere and stirred for 20 hours at ambient temperature. After neutralising with 0.6 ml 1-molar hydrochloric acid the reaction mixture is evaporated down i. vac., the residue is taken up in sat. sodium chloride solution and extracted with ethyl acetate. The combined organic phases are washed with sat. sodium chloride solution, dried over sodium sulphate and evaporated down i. vac. The residue is purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate=4:1).

Workup

  1. additionare added under an argon atmosphere
  2. customis evaporated down i
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases are washed with sat. sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated down i
  7. customThe residue is purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-198e62097ab64a0dac63cffb0a7eab82
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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