Acetyl chloride → HCID 67401253, compound

HRID 471713Notes

Reaction equation

HRID 471713 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-8d2a0c5fbd504599abeac33d910fbe6f
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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