Water → HCID 59139370, compound

HRID 2061135Notes

Reaction equation

HRID 2061135 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:11][C:12]1[C:13]([O:34][C:35](=[O:39])[N:36]([CH3:38])[CH3:37])=[CH:14][C:15]2[O:20][C:19](=[O:21])[C:18]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)=[C:17]([CH3:32])[C:16]=2[CH:33]=1.[C:40](Cl)(=[O:42])[CH3:41].O>C1COCC1>[Cl:11][C:12]1[C:13]([O:34][C:35](=[O:39])[N:36]([CH3:37])[CH3:38])=[CH:14][C:15]2[O:20][C:19](=[O:21])[C:18]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)=[C:17]([CH2:32][C:40](=[O:42])[CH3:41])[C:16]=2[CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 59139485HCID 59139485, compound

Product 1

HCID 59139370HCID 59139370, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

LiHMDS (11.5 mL, 1.0 M in THF) was added under nitrogen atmosphere at −78° C. to a suspension of dimethylcarbamic acid 6-chloro-4-methyl-3-(3-nitrobenzyl)-2-oxo-2H-1-benzopyran-7-yl ester (compound 1g-1-3) (4.0 g, 9.60 mmol) in anhydrous THF (100 mL), and the mixture was stirred at −78° C. for 30 minutes and at 0° C. for 30 minutes. Acetyl chloride (1.36 mL, 19.2 mmol) was then added thereto, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. A crude solid was obtained by vacuum concentration, and purified by column chromatography (ethyl acetate:hexane=1:3) to yield the title compound (1.28 g, 29%) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. customA crude solid was obtained by vacuum concentration
  7. custompurified by column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-9bbe0cad5a1e41fb9fe454fe0d0f44e4
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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