Pyridine → HCID 66781708, compound

HRID 1096721Notes

Reaction equation

HRID 1096721 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:14][CH:13]2[CH:12]([OH:15])[CH2:11][CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8].N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:14][CH:13]2[C:12](=[O:15])[CH2:11][CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 59779153HCID 59779153, compound

Product 1

HCID 66781708HCID 66781708, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-2-ol (455 mg, 1.88 mmol) in CH2Cl2 (10 mL) at 0° C. was treated with pyridine (0.38 mL, 4.6 mmol), followed by Dess-Martin periodinane (1.95 g, 4.6 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 (200 mg, 44%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.45-1.50 (m, 1 H) 1.51-1.58 (m, 1 H) 2.11 (dd, 1 H) 2.21-2.37 (m, 3 H) 2.37-2.45 (m, 1 H) 7.04 (dd, 1H) 7.32 (d, 1 H) 7.37 (d, 1 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-aca2891877604b0dbd1ab8e10041be4b
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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