Hydrochloric Acid → Benzyl 1-hydroxycyclopropanecarboxylate

HRID 1392782Notes

Reaction equation

HRID 1392782 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>[OH:16][C:17]1([C:20]([O:22][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:21])[CH2:19][CH2:18]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-hydroxycyclopropane-carboxylic acid (409 mg) in tetrahydrofuran (3.0 ml), and the mixture was stirred at room temperature for 23 hours. Methylene chloride and 1N hydrochloric acid were added to the reaction mixture to separate the mixture into two layers. An organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. A crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=41) to obtain the title compound (607 mg).

Workup

  1. customto separate the mixture into two layers
  2. washAn organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customA crude product was purified by column chromatography on silica gel (hexane:ethyl acetate=41)

Sources & evidence

ORD record
ord-d32bb401f86c4ce6ae6204cdf48301d7
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

Loading…