Carbon Dioxide → HCID 19261789, compound

HRID 556123Notes

Reaction equation

HRID 556123 reaction equation
[Mg].II.Br[CH2:5][CH2:6]Br.C(Br)=C.C(=O)=O.[C:14]1([C:20]2[CH:35]=[CH:34][C:23]3[C:24](=[O:33])[C:25]4[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=4[CH2:27][CH2:28][C:22]=3[CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[C:14]1([C:20]2[CH:35]=[CH:34][C:23]3[C:24]([CH:5]=[CH2:6])([OH:33])[C:25]4[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=4[CH2:27][CH2:28][C:22]=3[CH:21]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

9

Reactant 7

HCID 280Carbon DioxideHCID 807IodineHCID 78391,2-DibromoethaneHCID 11641Bromoethene2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 19261782HCID 19261782, compound

Product 1

HCID 19261789HCID 19261789, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
35 °C

Procedure

Magnesium turnings (0.45 g, 18.5 mmol) under tetrahydrofuran (5 mL) was activated with grain of iodine and with 1,2-dibromoethane (0.25 mL) and after the reaction was over, a solution of vinyl bromide (2.0 g, 18.5 mmol) in tetrahydrofuran (30 mL) was added (dry ice condenser, nitrogen atmosphere). The reaction start immediately and the remaining part of the vinyl bromide solution was added dropwise under stirring at such a rate as to maintain the mixture under reflux (30 min). The mixture was stirred at 65° C. for next 30 min, cooled to 35° C. and then over 30 min a solution of the above ketone (1.75 g, 6.15 mmol) in tetrahydrofuran (35 mL) was added dropwise. The mixture was stirred at 35° C. for 3 h and then poured on a mixture of crushed ice (100 g) and 25% solution of ammonium chloride (30 mL). The mixture was extracted with diethyl ether (50 mL, 2×20 mL), combined organic solutions were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue (2.5 g) was purified by flash-chromatography on silica gel (Fluka 60, 80 g, hexane/benzene 6:4) to yield 1.65 g (86%) of 2-phenyl-5-vinyl-10,11 dihydro-5H-dibenzo[a,d]cyclohepten-5-ol.

Workup

  1. temperatureto maintain the mixture
  2. temperatureunder reflux (30 min)
  3. stirringThe mixture was stirred at 65° C. for next 30 min
  4. stirringThe mixture was stirred at 35° C. for 3 h
  5. extractionThe mixture was extracted with diethyl ether (50 mL, 2×20 mL)
  6. washwere washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residue (2.5 g) was purified by flash-chromatography on silica gel (Fluka 60, 80 g, hexane/benzene 6:4)

Sources & evidence

ORD record
ord-2027f431960041619459f1bdfe329e5f
Source dataset
uspto-grants-2011_11
Patent number
US08053598B2

Reaction notes

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