Triacetoxyperiodinane → HCID 58954812, compound

HRID 333271Notes

Reaction equation

HRID 333271 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:15]([OH:17])[CH3:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15](=[O:17])[CH3:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58954783HCID 58954783, compound

Product 1

HCID 58954812HCID 58954812, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 1-(1-(3,4-dichlorophenyl)cyclohexyl)ethanol (494 mg, 1.81 mmol) in CH2Cl2 (18 mL) was added Dess-Martin periodinane (997 mg, 2.35 mmol). The resulting suspension was stirred at RT for 2 h and was then concentrated. The crude ketone was purified by silica gel column chromatography with an EtOAc/hexane gradient (product Rf=0.6 in 10% EtOAc/hexanes) to give 1-(1-(3,4-dichlorophenyl)cyclohexyl)ethanone (312 mg, 67%) as an orange oil. HPLC Rt=11.61 min; 1H NMR (400 mHz, CDCl3) 7.42-7.40 (m, 2H), 7.15 (dd, J=2.2, 8.4 Hz, 1H), 2.32-2.29 (m, 2H), 1.92 (s, 3H), 1.80-1.74 (m, 2H), 1.65-1.43 (m, 5H), 1.35-1.30 (m, 1H); 13C NMR (100 mHz, CDCl3) 209.5, 143.3, 133.2, 131.3, 130.9, 128.9, 126.3, 56.2, 33.7, 25.8 (2 overlapping peaks), 23.2.

Workup

  1. concentrationwas then concentrated
  2. customThe crude ketone was purified by silica gel column chromatography with an EtOAc/hexane gradient (product Rf=0.6 in 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5724e23e1b054f53881411d3ddf649f2
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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