HCID 14272244, compound → HCID 21703655, compound

HRID 1106973Notes

Reaction equation

HRID 1106973 reaction equation
[O:1]1[CH:3]2[C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:2]12.Br[Mg][CH2:19][CH:20]=[CH2:21]>O1CCCC1>[CH2:21]([CH:2]1[CH:3]([OH:1])[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2)[CH:20]=[CH2:19]

Participants

4

Reactant 2

HCID 14272244HCID 14272244, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 21703655HCID 21703655, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1a,10b-dihydro-6H-dibenzo[3,4:6,7]cyclohept[1,2-b]oxirene (1 g) was dissolved in 15 ml tetrahydrofuran and cooled to 0° C., under N2 atmosphere. Bromo-2-propenyl-magnesium (5,2 ml, 1M in tetrahydrofuran) was added dropwise to the mixture and the mixture was stirred at room temperature and then at 60° C. for two hours. The mixture was cooled to room temperature and quenched with 10% NH4Cl and water, dried and the solvent was evaporated, yielding 0.5 g (48%) of 10,11-dihydro-11-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-10-ol (interm. 4).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with 10% NH4Cl and water
  3. customdried
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-afda5755a9af4f4086d034e2270a3592
Source dataset
uspto-grants-2000_05
Patent number
US06057441

Reaction notes

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