Water → 2-(1-cyclopropylethoxy)Acetic acid

HRID 1106602Notes

Reaction equation

HRID 1106602 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([OH:7])=[O:6].[CH3:8][CH:9]([CH:11]1[CH2:13][CH2:12]1)[OH:10].O>C1COCC1>[CH:11]1([CH:9]([O:10][CH2:4][C:5]([OH:7])=[O:6])[CH3:8])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 791041-Cyclopropylethanol

Product 1

HCID 221142352-(1-cyclopropylethoxy)Acetic acidYield 29.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of NaH (80% in oil) (15.7 g, 523 mmol) in THF (180 mL) at 0° C. were added bromoacetic acid (28.0 g, 203 mmol) and a-methylcyclopropane methanol (10.0 g, 116 mmol). The resulting mixture was then stirred at 70° C. After a period of 18 h, the reaction mixture was poured over cold H2O and the H2O phase was extracted once with Et2O. The water phase was acidified with HCl and extracted twice with Et2O. The ether was dried over MgSO4, filtered and evaporated under reduced pressure. The crude oil was then purified by flash chromatography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH) to provide 5.0 g of the title compound.

Workup

  1. extractionthe H2O phase was extracted once with Et2O
  2. extractionextracted twice with Et2O
  3. dry with materialThe ether was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude oil was then purified by flash chromatography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH)

Sources & evidence

ORD record
ord-5edb3ae5209142688f3061d56bf20a0e
Source dataset
uspto-grants-2000_05
Patent number
US06057319

Reaction notes

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