Boron trifluoride etherate → 3-Cyclopentyl-2-methoxy-3-oxo-propionic acid methyl ester

HRID 1962214

Reaction equation

HRID 1962214 reaction equation
[C:1](O)(=[O:3])C.C(O)(=O)C.I(C1C=CC=CC=1)=O.B(F)(F)F.CCOCC.[CH2:26]([O:28][C:29](=[O:38])[CH2:30][C:31]([CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:32])C>CO>[CH3:26][O:28][C:29](=[O:38])[CH:30]([O:3][CH3:1])[C:31]([CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:32]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 11159709Ethyl 3-cyclopentyl-3-oxopropanoateHCID 73357407Acetic acid;iodosylbenzene

Product 1

HCID 597772863-Cyclopentyl-2-methoxy-3-oxo-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared using a method analogous to that described in Tetrahedron 1998, 44, 1603-1607: To a suspension of iodosobenzene diacetate (5.2 g, 16.3 mmol) in MeOH (40 mL) was added BF3.OEt2 (2.1 mL, 16.3 mmol). The resulting mixture was added to 3-cyclopentyl-3-oxo-propionic acid ethyl ester (3.0 g, 16.3 mmol) and stirred at rt overnight. The mixture was concentrated to half the total volume, quenched with satd. aq. NaHCO3, and extracted with CHCl3 (2×). The combined organic layers were dried and concentrated and the crude residue purified (EtOAc/hexanes) to yield a colorless oil (1.5 g, 43%). 1H NMR (MeOD): 4.4 (s, 1H), 3.8 (s, 3H), 3.5 (s, 3H), 3.3-3.2 (m, 1H), 1.9-1.5 (m, 8H).

Workup

  1. concentrationThe mixture was concentrated to half the total volume
  2. customquenched with satd
  3. extractionaq. NaHCO3, and extracted with CHCl3 (2×)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customthe crude residue purified (EtOAc/hexanes)

Sources & evidence

ORD record
ord-ad24e586c5144c8b9edf1c2ab1625b27
Source dataset
uspto-grants-2013_04
Patent number
US08415366B2

Linked notes

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