Diethyl Ether → HCID 58557114, compound

HRID 1969563Notes

Reaction equation

HRID 1969563 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([CH2:8][OH:9])[CH2:6][CH:5]([OH:10])[CH2:4]1)[CH3:2].Br([O-])(=O)=O.[K+].CCOCC>CC#N.O.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>[CH2:1]([C@H:3]1[C@@H:7]([CH2:8][OH:9])[CH2:6][C:5](=[O:10])[CH2:4]1)[CH3:2]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 23673461Potassium BromateHCID 58557273HCID 58557273, compound

Product 1

HCID 58557114HCID 58557114, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 180504Ceric ammonium nitrateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentanol (4.00 g, 27.7 mmol) in MeCN (70 mL) and water (30.0 mL) was added potassium bromate (1.487 mL, 29.1 mmol) and CAN (0.760 g, 1.387 mmol). The reaction mixture was heated to about 80° C. After about 2 h, the reaction mixture was cooled to rt and Et2O (100 mL) was added. The organic layer was separated, washed with brine (30 mL), concd in vacuo and purified by chromatography on silica gel eluting with EtOAc/heptane (20-60%) to provide (3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentanone (2.4 g, 61%) as an oil. 1H NMR (400 MHz, CDCl3) δ 3.79 (dd, J=10.5, 5.3 Hz, 1H), 3.70 (dd, J=10.5, 6.5 Hz, 1H), 2.55-2.44 (m, 1H), 2.41-2.25 (m, 4H), 2.15-2.05 (m, 1H), 1.55-1.65 (m, 2H), 1.43-1.30 (m, 1H), 0.97 (t, J=7.3 Hz, 3H).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. customThe organic layer was separated
  3. washwashed with brine (30 mL), concd in vacuo
  4. custompurified by chromatography on silica gel eluting with EtOAc/heptane (20-60%)

Sources & evidence

ORD record
ord-3956f9f31364426eb0a611f3f4748fca
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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