Triethylamine → HCID 22989978, compound

HRID 1169478Notes

Reaction equation

HRID 1169478 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:15]B(O)O)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH3:14].O[C:20]1[CH:21]=[CH:22][C:23]2[S:29](=[O:31])(=[O:30])[CH2:28][CH2:27][C:26]([C:32]([O:34][CH3:35])=[O:33])=[CH:25][C:24]=2[CH:36]=1.C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH3:14])[O:15][C:20]1[CH:21]=[CH:22][C:23]2[S:29](=[O:31])(=[O:30])[CH2:28][CH2:27][C:26]([C:32]([O:34][CH3:35])=[O:33])=[CH:25][C:24]=2[CH:36]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22989977Methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylateHCID 22990216HCID 22990216, compound

Product 1

HCID 22989978HCID 22989978, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-methyl-4-propoxyethoxyphenylboric acid (710 mg), methyl 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (400 mg) and cupric acetate (270 mg) suspended in dichloromethane (15 ml) was added triethylamine (1.04 ml). The resulting mixture was stirred for one day with a calcium chloride tube attached to the reaction vessel, was then mixed with celite and was filtered to remove an insoluble material. The filtrate was concentrated and the residue was subjected to purification using silica gel column chromatography to obtain methyl 7-[3-methyl-4-(2-propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (475 mg) as a brown oily substance.

Workup

  1. additionwas then mixed with celite
  2. filtrationwas filtered
  3. customto remove an insoluble material
  4. concentrationThe filtrate was concentrated
  5. customthe residue was subjected to purification

Sources & evidence

ORD record
ord-e8e77280faa24e8cafa2dce4042eb60e
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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