Benzoyl chloride → HCID 67418524, compound

HRID 1056905Notes

Reaction equation

HRID 1056905 reaction equation
[C:1]([O:4][C:5]([C:9](=[O:11])[CH3:10])=[CH:6][O:7][CH3:8])(=[O:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1.C1(C)C=CC=CC=1>[C:1]([O:4][C:5]([C:9](=[O:11])[CH2:10][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:6][O:7][CH3:8])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 538084841-Methoxy-3-oxobut-1-en-2-yl acetate

Product 1

HCID 67418524HCID 67418524, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 545 mg (3.5 mmol) of 1-methoxy-3-oxobut-1-en-2-yl acetate in THF (14.2 mL) −78° C. was added LHMDS (3.45 mL of a 1 M solution in toluene) dropwise. After stirring for 20 min at −78° C., the reaction mixture was treated with 0.4 mL (3.5 mmol) of benzoyl chloride dropwise, then removed from the cold bath and allowed to warm to room temperature and continue stirring for 18 h. The reaction was quenched with 10 mL 10% aq HCl and extracted with diethyl ether (3×10 mL). The organic fractions were combined, washed with sat. aq. NaCl, dried (Na2S0), and concentrated under reduced pressure to provide 1-methoxy-3,5-dioxo-5-phenylpent-1-en-2-yl acetate which was used the subsequent step without further purification.

Workup

  1. customremoved from the cold bath
  2. temperatureto warm to room temperature
  3. stirringcontinue stirring for 18 h
  4. customThe reaction was quenched with 10 mL 10% aq HCl
  5. extractionextracted with diethyl ether (3×10 mL)
  6. washwashed with sat. aq. NaCl
  7. customdried (Na2S0)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d51a32fc002476f9abef9bff0e3031e
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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