Pyridine → HCID 86743950, compound

HRID 1651072Notes

Reaction equation

HRID 1651072 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[CH:7]([CH2:16][OH:17])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:5]=2[CH:4]=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.N1C=CC=CC=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]2[CH:7]([CH2:16][O:17][S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=3)(=[O:28])=[O:27])[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 67794549HCID 67794549, compound

Product 1

HCID 86743950HCID 86743950, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-5-hydroxymethyldibenzo[a,d]cycloheptene (10.5 g) in dry dichloromethane (150 ml) was added p-toluenesulphonyl chloride (8.1 g), pyridine (6.6 g) and 4-dimethylamino pyridine (300 mg). The reaction mixture was refluxed for 15h, cooled, washed with water (2×200 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash silica chromatography using 15% ethyl acetate in hexane as eluent to give the title compound as an oil (13.5 g). δ(360 MHz, CDCl3), 2.44 (3H, s, Ar--CH3), 3.78 (3H, s, OCH3), 4.19-4.31 (3H, m CH-CH2 --OSO2Ar). 6.58 (1H, d, J=11.9 Hz, Ar--CH=CH--Ar), 6.65 (1H, d, J=11.9 Hz, Ar--CH=CH--Ar), 6.68 (1H, d, J=2.7, CH=C(OCH3)--CH), 6.85 (1H, dd, J=8.4 and 2.7 Hz, CH=C(OCH3)--CH) and 7.16-7.42 (9H, m, aromatics). m/e 406 (M+).

Workup

  1. temperaturecooled
  2. washwashed with water (2×200 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash silica chromatography

Sources & evidence

ORD record
ord-e92afd2ad4a44f599998a05e3b97542c
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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