Pyridine → HCID 86743949, compound

HRID 1651060Notes

Reaction equation

HRID 1651060 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[CH:6]([CH2:15][OH:16])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.N1C=CC=CC=1>ClCCl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[CH:6]([CH2:15][O:16][S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 67793754HCID 67793754, compound

Product 1

HCID 86743949HCID 86743949, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-hydroxymethyl-dibenzo [a,d]cycloheptene (6.1 g) in dry dichloromethane (60 ml) was added p-toluenesulphonyl chloride (4.9 g). pyridine (4 g) and 4-dimethylamino pyridine (100 mg). The reaction mixture was refluxed for 14 h, cooled, washed with water (2×50 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue. was purified by flash silica chromatography using 10% ethyl acetate in hexane as eluent to give the title compound as a colourless oil (8.2 g). δ (360 MHz, CDCl3) 2.46 (3H, s, CH3), 4.12 (1H, dd J=6.2 and 3.5 Hz, CH--CH2 --O), 4.24-4.32 (2H, m, CH--CH2 --O), 6.50 (1H, d, J=11.9 Hz, CHA =CHB), 6.73 (1H, d, J=11.9 Hz, CHA =CHB), 7.10-7.40 (11H, m, ArH).

Workup

  1. temperatureThe reaction mixture was refluxed for 14 h
  2. temperaturecooled
  3. washwashed with water (2×50 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customwas purified by flash silica chromatography

Sources & evidence

ORD record
ord-dfdbdfad2a394abbbbf266b2ce1017a1
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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