Hydrochloric Acid → Benzyl 1-hydroxycyclopropanecarboxylate

HRID 2104420Notes

Reaction equation

HRID 2104420 reaction equation
C(N(CC)CC)C.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH:16][C:17]1([C:20]([OH:22])=[O:21])[CH2:19][CH2:18]1.Cl>O1CCCC1.C(Cl)Cl>[CH2:8]([O:22][C:20]([C:17]1([OH:16])[CH2:19][CH2:18]1)=[O:21])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 27331601-Hydroxy-1-cyclopropanecarboxylic acid

Product 1

HCID 22934671Benzyl 1-hydroxycyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1.0 mL) and benzyl bromide (650 μL) were added to a solution of 1-hydroxycyclopropanecarboxylic acid (409 mg) in tetrahydrofuran (3.0 mL), and the mixture was stirred at room temperature for 23 hours. To the reaction mixture were added methylene chloride and 1N aqueous hydrochloric acid to thereby give two layers. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated brine, followed by drying over sodium sulfate, to thereby give a crude product. The crude product was subjected to purification through silica gel column chromatography (hexane:ethyl acetate=4:1), to thereby give the title compound (607 mg).

Workup

  1. customto thereby give two layers
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. dry with materialby drying over sodium sulfate
  4. customto thereby give a crude product
  5. customThe crude product was subjected to purification through silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-00e63e02203f4244a7671248019f15cf
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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