Dichloromethane → Methyl 7-(4-propylphenoxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 1169470Notes

Reaction equation

HRID 1169470 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1.[CH2:19]([C:22]1[CH:27]=[CH:26][C:25](OB(O)O)=[CH:24][CH:23]=1)[CH2:20][CH3:21].ClCCl>C(N(CC)CC)C>[CH2:19]([C:22]1[CH:27]=[CH:26][C:25]([O:1][C:2]2[CH:3]=[CH:4][C:5]3[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=3[CH:18]=2)=[CH:24][CH:23]=1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 21869456(4-Propylphenoxy)boronic acidHCID 22989977Methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 22990095Methyl 7-(4-propylphenoxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylateYield 69.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.40 g), 4-propylphenylboric acid (0.49 g), cupric acetate (0.27 g), MS 4A (0.8 g) and dichloromethane (15 ml) was added at room temperature triethylamine (1.04 ml), and the resulting mixture was stirred for 20 hours. The reaction mixture was filtered to remove an insoluble material and the filtrate was concentrated under reduced pressure. The residue was subjected to separation and purification using column chromatography (ethyl acetate:hexane 1:2) to obtain methyl 7-(4-propylphenoxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.40 g) as a light yellow, oily substance.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove an insoluble material
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was subjected to separation and purification

Sources & evidence

ORD record
ord-fe9631bd396a40d1b6daa870205cc77f
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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