Pyridine → HCID 59779113, compound

HRID 1096706Notes

Reaction equation

HRID 1096706 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]23[CH2:12][CH:11]2[CH:10]([OH:13])[CH2:9][CH2:8]3)=[CH:3][CH:2]=1.N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[C:1]1([CH3:14])[CH:2]=[CH:3][C:4]([C:7]23[CH2:12][CH:11]2[C:10](=[O:13])[CH2:9][CH2:8]3)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 59779158HCID 59779158, compound

Product 1

HCID 59779113HCID 59779113, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-p-tolyl-bicyclo[3.1.0]hexan-2-ol (1 g, 5.3 mmol) in CH2Cl2 (20 mL) was treated with pyridine (0.6 mL, 7.4 mmol) followed by Dess-Martin periodinane (2.7 g, 6.3 mmol) and warmed to ambient temperature. After 2 h, 3 drops of H2O were added. After 0.5 h, the reaction was quenched with saturated NaHCO3 saturated Na2SO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried and concentrated in vacuo. Purification by silica gel chromatography gave the target compound (760 mg, 77%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.42-1.47 (m, 1 H) 1.53-1.61 (m, 1 H) 2.06-2.11 (m, 1 H) 2.20-2.29 (m, 2 H) 2.30-2.36 (m, 1 H) 2.32-2.34 (m, 3 H) 2.37-2.45 (m, 1 H) 7.08-7.18 (m, 4 H).

Workup

  1. waitAfter 0.5 h
  2. customthe reaction was quenched with saturated NaHCO3 saturated Na2SO3
  3. extractionextracted with CH2Cl2 (3×)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-50c55c6dd5b446ff803919cf384ed850
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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