Pentane → HCID 66731474, compound

HRID 227823Notes

Reaction equation

HRID 227823 reaction equation
[C:1]([NH:5][C:6]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[CH3:18][CH2:19][CH2:20][CH2:21][CH3:22].C[O:24][CH2:25][CH2:26]OC>>[C:25]([C:12]1[CH:11]=[CH:10][O:9][C:8]=1[C:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])(=[O:24])[C:26]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 8003PentaneHCID 80711,2-Dimethoxyethane2×HCID 963338HCID 963338, compound2×HCID 178418306HCID 178418306, compound

Product 1

HCID 66731474HCID 66731474, compound

Procedure

To a stirring solution of N-tert-butylfuran-2-carboxamide (1.8 ml, 12 mmol) in 100 mL DME under argon at −78° C. was added tert-butyllithium, 1.7 M solution in pentane (14 ml, 24 mmol) slowly dropwise over 5 min. The heterogeneous reaction mixture was allowed to stir 1 h, at which point a solution of N-tert-butylfuran-2-carboxamide (1.8 ml, 12 mmol) in 10 mL DME was added over 5 min, dropwise. After 15 min, the bath was removed and the reaction was allowed to warm to ambient temperature. The reaction was quenched by addition of saturated aqueous ammonium chloride, water, and EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by silica gel chromatography, ISCO, 80 g, 0-40% EtOAc/hexanes over 33 min to give a semi-solid. This material was triturated 3× hexanes to give 3-benzoyl-N-tert-butylfuran-2-carboxamide as white crystals. MS m/z=272 [M+H]+. Calc'd for C16H17NO3: 271.3.

Workup

  1. additionwas added over 5 min
  2. customthe bath was removed
  3. customThe reaction was quenched by addition of saturated aqueous ammonium chloride, water, and EtOAc
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting material was purified by silica gel chromatography, ISCO, 80 g, 0-40% EtOAc/hexanes over 33 min
  8. customto give a semi-solid
  9. customThis material was triturated 3× hexanes

Sources & evidence

ORD record
ord-ab0b201f071a4c53ba2eac3bb8ad1856
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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