Diethyl Ether → HCID 53982839, compound

HRID 1651066Notes

Reaction equation

HRID 1651066 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[CH:8]=[C:7]([OH:17])[C:6]=2[CH:18]=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:3]=[CH:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[CH2:8][C:7](=[O:17])[C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724130Cornforth reagentHCID 67794506HCID 67794506, compound

Product 1

HCID 53982839HCID 53982839, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-5-hydroxy-dibenzo[a,e]cyclooctene (0.75 g) in dry dichloromethane (60 ml) was added pyridinium dichromate (2.1 g) and crushed 4 A molecular sieves (1.3 g). After stirring at room temperature for 14 h, diethyl ether (150 ml) Was added and the reaction mixture was filtered through a plug of celite. The solvent was removed and the residue purified by chromatography on flash silica with 5% ethyl acetate in hexane as eluent to give, as a colorless solid, the title compound (0.7 g). δ(360 MHz, CDCl3) 4.04 (2H, s, CH2 --C=O), 6.95 (1H, d, J=12.8 Hz, CHA =CHB), 7.09 (1H, d, J=12.8 Hz, CHA =CHB), 7.22-7.59 (6H, m, ArH), 8.36 (1H, d, J=2.2 Hz, C(O)--C=CH--CBr).

Workup

  1. customcrushed 4 A molecular sieves (1.3 g)
  2. filtrationthe reaction mixture was filtered through a plug of celite
  3. customThe solvent was removed
  4. customthe residue purified by chromatography on flash silica with 5% ethyl acetate in hexane as eluent
  5. customto give, as a colorless solid

Sources & evidence

ORD record
ord-accd569cd127403ba16a497536a71961
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

Loading…