4-tert-Butylbenzoyl chloride → tert-Butyl phenyl ketone

HRID 2119779Notes

Reaction equation

HRID 2119779 reaction equation
C([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)(C)(C)C>N1C=CC=CC=1>[C:8]([C:9]([C:8]1[CH:7]=[CH:6][CH:5]=[CH:13][CH:12]=1)=[O:10])([CH3:12])([CH3:9])[CH3:7]

Participants

3

Reactant 1

HCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 70308tert-Butyl phenyl ketone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2′-Deoxy-2′-N-phthaloyl derivative (21a) (5.4 g, 8.45 mmol) was dissolved in anhydrous pyridine and 4-tert-butylbenzoyl chloride (1.2 eq) was added at 0° C. and the reaction mixture left overnight at room temperature. The reaction was subsequently quenched with methanol (10 mL), solvents removed in vacuo and the residue dissolved in toluene and evaporated to dryness. The resulting oil was dissolved in dichloromethane, washed with saturated aq. NaHCO3 and brine, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica, using EtOAc-Hexanes (1:2) mixture as an eluent to give 5.06 g (75%) of the fully protected synthon (22a, R=t-BuBz).

Workup

  1. customThe reaction was subsequently quenched with methanol (10 mL), solvents
  2. customremoved in vacuo
  3. dissolutionthe residue dissolved in toluene
  4. customevaporated to dryness
  5. dissolutionThe resulting oil was dissolved in dichloromethane
  6. washwashed with saturated aq. NaHCO3 and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-654529dbf2904f3d885020534f956aad
Source dataset
uspto-grants-2004_02
Patent number
US06686463B2

Reaction notes

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