Pyridine → HCID 22395366, compound

HRID 1019267Notes

Reaction equation

HRID 1019267 reaction equation
[OH:1][C:2]1([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:22]([O:1][C:2]1([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[CH2:3][CH2:4][C:5](=[O:8])[CH2:6][CH2:7]1)(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 223953644-(4-Fluorophenyl)-4-hydroxycyclohexan-1-one

Product 1

HCID 22395366HCID 22395366, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-hydroxy-4-(4-fluorophenyl)cyclohexanone (520 mg, 2.5 mmol), pyridine (2 ml) and 4-dimethylaminopyridine (46 mg) in CH2Cl2 (25 ml) at 0° C. was added dropwise a solution of acetic anhydride (1 ml) in CH2Cl2 (5 ml). The mixture was warmed to room temperature and stirred for 28 h before being quenched with water (30 ml). The organic phase was washed with 1 M HCl (2×30 ml) and brine (30 ml), dried over MgSO3, and concentrated in vacuo. The residue was purified by flash chromatography (25% ether in petroleum ether) to afford the desired ketone (510 mg, 82%) as a colorless solid. mp 113-115° C. 1H NMR (500 MHz, CDCl3) δ2.11 (s, 3H), 2.20 (m, 2H), 2.43 (m, 2H), 2.68 (m, 2H), 2.86 (m, 2H), 7.05 (t, J=8.3, 2H), 7.35-7.38 (m, 2H).

Workup

  1. custombefore being quenched with water (30 ml)
  2. washThe organic phase was washed with 1 M HCl (2×30 ml) and brine (30 ml)
  3. dry with materialdried over MgSO3
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (25% ether in petroleum ether)

Sources & evidence

ORD record
ord-d7933de38be844b68ac02b9a75ada250
Source dataset
uspto-grants-2002_11
Patent number
US06486199B1

Reaction notes

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