Dimethylformamide → HCID 18348621, compound

HRID 2268499Notes

Reaction equation

HRID 2268499 reaction equation
I[CH2:2][CH2:3][CH:4]1[CH2:10][CH2:9][C:8]2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]([O:17][CH3:18])=[C:14]([O:15][CH3:16])[C:7]=2[CH2:6][CH2:5]1.[OH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[C:30]1([C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:2][CH2:3][CH:4]3[CH2:10][CH2:9][C:8]4[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]([O:17][CH3:18])=[C:14]([O:15][CH3:16])[C:7]=4[CH2:6][CH2:5]3)=[CH:29][CH:28]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 183485187-(2-Iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene

Product 1

HCID 18348621HCID 18348621, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 7-(2-iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene(1.64 g),4-hydroxybiphenyl (797 mg), potassium carbonate (1.08 g), and DMF (16 ml) was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by alumina column chromatography (toluene) to yield the entitled compound (1.73 g) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by alumina column chromatography (toluene)

Sources & evidence

ORD record
ord-bc3ae9cbb5634e62a243de79fb17b0ce
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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