Hydrochloric Acid → HCID 86756706, compound

HRID 1977517Notes

Reaction equation

HRID 1977517 reaction equation
C[Mg+].[Br-].C1([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH2:12][CH:13]([CH2:20][CH2:21][CH:22]2[CH2:30][C:29]4[C:24](=[CH:25]C=CC=4C4C=CC=CC=4)[C:23]2=O)[C:14]3=O)C=CC=CC=1.Cl.[CH2:39]1[CH2:43]O[CH2:41][CH2:40]1>CCOCC>[CH3:41][C:40]1([CH:12]2[C:11]3[C:10](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:14]=[C:13]2[CH2:20][CH2:21][C:22]2[CH:30]([C:11]3([CH3:12])[CH:10]=[CH:18][CH:17]=[CH:16][CH2:15]3)[C:29]3[C:24]([CH:23]=2)=[CH:25][CH:14]=[CH:13][CH:20]=3)[CH:21]=[CH:22][CH:23]=[CH:43][CH2:39]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 15913972HCID 15913972, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 86756706HCID 86756706, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 67.8 mL MeMgBr (3M in ether) in 100 mL Et2O was added a solution of 15 g (33.9 mmol) of 1,2-bis(4-phenyl-indanonyl)ethane, prepared as described in the above synthesis 8(a), in 150 mL THF, over a period of 45 minutes, at 0° C. The formation of a white/beige precipitate was observed. The reaction mixture was allowed to warm to 20° C. and was maintained under stirring for 2 hours. The reaction mixture was then poured into ice and acidified to pH 1, with 37% HCl, and finally extracted with Et2O. The organic layer was extracted with a saturated solution of NaCl and the solvent was removed in vacuum. The formed diol was dissolved in CH2Cl2 and ptoluene-sulfonic acid was added. The mixture was stirred overnight at 20° C. The solution was dried over MgSO4, filtered and the solvent was removed in vacuum, thus yielding 9.0 g of the ligand 1,2-bis(l-methyl-phenyl-2-indenyl)ethane (69% yield).

Workup

  1. customprepared
  2. temperaturewas maintained
  3. additionThe reaction mixture was then poured into ice
  4. extractionfinally extracted with Et2O
  5. extractionThe organic layer was extracted with a saturated solution of NaCl
  6. customthe solvent was removed in vacuum
  7. dissolutionThe formed diol was dissolved in CH2Cl2
  8. additionptoluene-sulfonic acid was added
  9. stirringThe mixture was stirred overnight at 20° C
  10. dry with materialThe solution was dried over MgSO4
  11. filtrationfiltered
  12. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-79d5516c613a45e3b8ea6879965d6a47
Source dataset
uspto-grants-2001_05
Patent number
US06232484B1

Reaction notes

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