Water → HCID 15007585, compound

HRID 358607Notes

Reaction equation

HRID 358607 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([N:15]3[CH2:19][C:18]([O:20][CH2:21][CH3:22])=[CH:17][C:16]3=[O:23])[C:7]=2[CH:24]=1)#[N:2].N1C=CC=CC=1.[C:31](OC(=O)C)(=[O:33])[CH3:32].O>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[C@@H:9]([O:14][C:31](=[O:33])[CH3:32])[C@H:8]([N:15]3[CH2:19][C:18]([O:20][CH2:21][CH3:22])=[CH:17][C:16]3=[O:23])[C:7]=2[CH:24]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 15007582HCID 15007582, compound

Product 1

HCID 15007585HCID 15007585, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(4-ethoxy-2-oxo-3-pyrrolin-1-yl)-2H-1-benzopyran (0.5 g) in 25 ml of methylene chloride at 0° C. was added pyridine (0.415 g) and acetic anhydride (0.56 g), and the mixture stirred at room temperature for 5 days. The reaction mixture was then stirred with a mixture of 50 ml of water and 40 ml of methylene chloride. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate and solvent removed under reduced pressure. The residue was triturated with ether followed by pentane to give 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-acetyloxy-4-(4-ethoxy-2-oxo-3-pyrrolin-1-yl)-2H-1-benzopyran, m.p. 156° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate and solvent
  4. customremoved under reduced pressure
  5. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-52d0ecf3fad3410094c94548d16fc216
Source dataset
uspto-grants-1991_03
Patent number
US04997846

Reaction notes

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