Diethyl Ether → tert-Butyl 3-oxocyclopentane-1-carboxylate

HRID 1367494Notes

Reaction equation

HRID 1367494 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[C:10](O)([CH3:13])([CH3:12])[CH3:11].C(OCC)C>CN(C)C1C=CN=CC=1.ClCCl>[C:10]([O:8][C:7]([CH:4]1[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]1)=[O:9])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6386tert-ButanolHCID 2277983-Oxocyclopentanecarboxylic acid

Product 1

HCID 14009986tert-Butyl 3-oxocyclopentane-1-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2 °C

Procedure

To a cold (ice bath) solution of 3-oxo-1-cyclopentanecarboxylic acid (1.50 g), tert-butylalcohol (1.05 g) and 4-dimethylaminopyridine (140 mg) in dichloromethane (9 mL) was added a solution of dicyclocarbodiimide in dichloromethane (9 mL). The mixture was stirred 3 hours at ca. 2° C. then diethylether (30 mL) was added and the precipitate was filtered off and discarded. The solution was concentrated in vacuo. The residue was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (9:1 v/v) as eluant to afford the title compound (1.80 g, 96%) as colorless oil. MS (EI): 111 (M-OtBu.)+.

Workup

  1. filtrationthe precipitate was filtered off
  2. concentrationThe solution was concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (9:1 v/v) as eluant

Sources & evidence

ORD record
ord-cd421189375b431ca283a94321e025c6
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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