Diethyl Ether → HCID 54522175, compound

HRID 1651062Notes

Reaction equation

HRID 1651062 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]([OH:16])=[CH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:4]=2[CH:3]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OCC)C>ClCCl>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6](=[O:16])[CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH:10]=[CH:11][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724130Cornforth reagentHCID 67793788HCID 67793788, compound

Product 1

HCID 54522175HCID 54522175, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-hydroxy-dibenzo[a,e]cyclooctene (2.3 g) in dry dichloromethane (100 ml) was added pyridinium dichromate (5.75 g) and crushed 4 A molecular sieves (3 g). After stirring at room temperature for 14 h, diethyl ether (200 ml) was added and the reaction mixture was filtered through a plug of celite. The solvent was removed in vacuo and the residue purified by chromotagraphy on flash silica with 5% ethyl acetate in hexane as eluent to give as a colourless solid. the title compound (2.1 g, m.p. 121°-123° C.). δ (360 MHz, CDCl3) 4.03 (2H, s, CH2), 6.92 (1H, d, J=12.8 Hz, CHA =CHB), 7.09 (1H, d, J=12.8 Hz, CHa =CHB), 7.20-7.56 (6H, m, ArH), 8.08 (1H, d, J=8.5 Hz, BrC=CH--CH= C--C=O). m/e 300 and 298 (M+).

Workup

  1. customcrushed 4 A molecular sieves (3 g)
  2. filtrationthe reaction mixture was filtered through a plug of celite
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by chromotagraphy on flash silica with 5% ethyl acetate in hexane as eluent
  5. customto give as a colourless solid

Sources & evidence

ORD record
ord-172446f99a2043488b5934ca2230f8dd
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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