Pyridine → 5-(Naphthalen-2-yl)bicyclo[3.1.0]hexan-2-one

HRID 1096741Notes

Reaction equation

HRID 1096741 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]12[CH2:16][CH:15]1[CH:14]([OH:17])[CH2:13][CH2:12]2.N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]12[CH2:16][CH:15]1[C:14](=[O:17])[CH2:13][CH2:12]2

Participants

6

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 597791155-(Naphthalen-2-yl)bicyclo[3.1.0]hexan-2-ol

Product 1

HCID 597791645-(Naphthalen-2-yl)bicyclo[3.1.0]hexan-2-oneYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(naphthalen-2-yl)bicyclo[3.1.0]hexan-2-ol (2.35 g, 10.5 mmol) in dichloromethane (110 mL) was treated with pyridine (1.18 mL, 14.6 mmol, 1.4 eq.) followed by Dess-Martin periodinane (5.34 g, 12.6 mmol, 1.2 eq.) and warmed to ambient temperature. After 2 h, 3 drops of water were added. After 0.5 h, the reaction was quenched with saturated sodium hydrogen carbonate (50 mL), saturated sodium sulphite (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic extracts was dried over magnesium sulphate and concentrated in vacuo. Purification by silica gel chromatography using 1:6 ethyl acetate/petrol as the eluting solvent afforded the desired compound (1.44 g, 62%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.56-1.58 (1H, m, CH), 1.71-1.75 (1H, m, CH), 2.22-2.25 (1H, m, CH), 2.30-2.34 (2H, m, CH2), 2.44-2.57 (2H, m CH2), 7.34 (1H, dd, J 1.9, 8.5, ArH), 7.44-7.51 (2H, m, ArH), 7.72-7.73 (1H, m, ArH), 7.80-7.83 (3H, m, ArH).

Workup

  1. waitAfter 0.5 h
  2. customthe reaction was quenched with saturated sodium hydrogen carbonate (50 mL), saturated sodium sulphite (50 mL)
  3. extractionextracted with dichloromethane (3×50 mL)
  4. dry with materialThe combined organic extracts was dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-3d1f553bf812440ba1a4b680849f623f
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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