Iodine → 1,2,3,4-Tetrahydro-1,4a,9b-trimethyl-1,4methanodibenzofuran-8-carbaldehyde

HRID 1289144Notes

Reaction equation

HRID 1289144 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3([CH3:16])[CH:10]4[CH2:14][C:13]([CH3:15])([C:7]3([CH3:17])[C:6]=2[CH:18]=1)[CH2:12][CH2:11]4.[Mg].II.[O:22]1CCC[CH2:23]1>>[CH3:15][C:13]12[CH2:14][CH:10]([C:8]3([CH3:16])[C:7]1([CH3:17])[C:6]1[CH:18]=[C:2]([CH:23]=[O:22])[CH:3]=[CH:4][C:5]=1[O:9]3)[CH2:11][CH2:12]2

Participants

5

Reactant 4

HCID 807IodineHCID 8028TetrahydrofuranHCID 5462224MagnesiumHCID 18925573HCID 18925573, compound

Product 1

HCID 214595761,2,3,4-Tetrahydro-1,4a,9b-trimethyl-1,4methanodibenzofuran-8-carbaldehydeYield 74%

Procedure

13.76 g (44.8 mmol) of 8-bromo-THTMDBF obtained in Example 2 were added dropwise into a three-necked flask under nitrogen containing 1.31 g of magnesium and an iodine crystal in 5 ml of tetrahydrofuran, and the mixture was maintained under reflux for 2 h, 30 min. After the magnesium was filtered off, the reaction medium was poured into ice-cold water, acidified to pH 1 with concentrated hydrochloric acid and extracted with ether. The organic phase was washed with water, dried over magnesium sulfate, filtered and evaporated to yield 8.47 g (74%) of the expected compound, melting at 144.7° C.; αD =-7° (c=1, chloroform).

Workup

  1. temperatureunder reflux for 2 h, 30 min
  2. filtrationAfter the magnesium was filtered off
  3. additionthe reaction medium was poured into ice-cold water
  4. extractionextracted with ether
  5. washThe organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ed06ccd494ba4e379492f97a9387ab37
Source dataset
uspto-grants-1998_05
Patent number
US05747530

Reaction notes

Loading…