Acetyl chloride → HCID 67401253, compound

HRID 711850Notes

Reaction equation

HRID 711850 reaction equation
[OH:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:7]=1[C:8]#[N:9].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27]>CN(C1C=CN=CC=1)C.ClCCl.CCOC(C)=O>[C:26]([O:1][C:2]([CH3:18])([CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:7]=1[C:8]#[N:9])[CH3:17])(=[O:28])[CH3:27]

Participants

7

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67400326HCID 67400326, compound

Product 1

HCID 67401253HCID 67401253, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3-hydroxy-3-methylbutoxy)-6-nitrobenzonitrile (Example 231d) (250 mg, 1 mmol), triethylamine (3 equiv.), and DMAP (0.1 equiv.) in dry dichloromethane (20 mL) was added dropwise acetyl chloride (1.5 equiv.) at 0° C. under nitrogen. The reaction mixture was then stirred at 0° C.—room temperature overnight. The reaction was diluted with EtOAc, washed with brine, and dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel eluting with 20% EtOAc in hexanes to give the title compound (137 mg, 47%). MS 293 (MH+).

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by chromatography on silica gel eluting with 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-36ad0a7ed5804fc59b9e9ab41f48a139
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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