Water → HCID 11514883, compound

HRID 418866Notes

Reaction equation

HRID 418866 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:15]([C:16](=[O:18])[CH:17]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[CH3:19][C:20](OC(C)=O)=[O:21].CCN(CC)CC.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:20]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:15]([C:16](=[O:18])[CH:17]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1)(=[O:21])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 10491161HCID 10491161, compound

Product 1

HCID 11514883HCID 11514883, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer were placed 2-(4-hydroxy-phenyl)-thiochromen-4-one (1.298 g, 5.1 mmol), Ac2O (625 mg, 6.12 mmol), Et3N (619 mg, 6.12 mmol) and catalytic amount of DMAP in DCM (10 mL) and the reaction mixture was stirred for 24 h at rt. The reaction mixture was poured into water and extracted with EtOAc. The organic layer washed with water, dried and concentrated to afford the 2-(4-acetoxy-phenyl)-thiochromen-4-one (1.4 g, 96%).

Workup

  1. customIn a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer
  2. extractionextracted with EtOAc
  3. washThe organic layer washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac005eb2113545339e604c4a087e0bb0
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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