Benzyl Bromide → HCID 59434260, compound

HRID 1987533Notes

Reaction equation

HRID 1987533 reaction equation
[CH3:1][Si:2]([CH3:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:3]1[C@@H:7]([CH2:8][OH:9])[C:6]([CH2:10][O:11]C(OC)(C)C)=[CH:5][CH2:4]1.[H-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.N12CCNC=C1CCCC=C2>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH3:23][Si:2]([CH3:1])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C@@H:3]1[C@@H:7]([CH2:8][O:9][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:6]([CH2:10][OH:11])=[CH:5][CH2:4]1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22177674HCID 22177674, compoundHCID 68838660(1R,5S)-5-(Dimethylphenylsilyl)-2-[(1-methoxy-1-methylethoxy)methyl]-2-cyclopentene-1-methanol

Product 1

HCID 59434260HCID 59434260, compoundYield 119.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a 250-mL 3-necked round bottomed flask equipped with a mechanical stirrer and a thermometer was charged 75 (35 g, 0.1 moles) and THF (60 mL) under an atmosphere of argon. NaH (6 g, 60%, mineral oil suspension, 0.15 moles) was added to the solution. The mixture was heated at 60° C. for 1 hour and then cooled to room temperature. Benzyl bromide (23.8 mL, 0.2 moles) and tetrabutylammonium bromide (10 g, 0.03 moles) were added to the suspension. The reaction mixture was heated at 70° C. for 6 hours and then the reaction mixture was cooled to room temperature. 1,9-diazabicyclo[5.4.0]undecen-7-ene (45 mL, 0.2 moles) was added and heated at 50° C. for 45 min. The reaction mixture was cooled to room temperature, quenched with 1N HCl to pH ˜1 and extracted with a mixture of EtOAc-hexane (250 mL). The organic layer was washed with water (500 mL), brine (100 mL) and concentrated in vacuo to afford the title compound (42 g) as a brown oil.

Workup

  1. customTo a 250-mL 3-necked round bottomed flask equipped with a mechanical stirrer
  2. temperaturecooled to room temperature
  3. temperatureThe reaction mixture was heated at 70° C. for 6 hours
  4. temperaturethe reaction mixture was cooled to room temperature
  5. temperatureheated at 50° C. for 45 min
  6. temperatureThe reaction mixture was cooled to room temperature
  7. customquenched with 1N HCl to pH ˜1
  8. extractionextracted with a mixture of EtOAc-hexane (250 mL)
  9. washThe organic layer was washed with water (500 mL), brine (100 mL)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67e7668fa1514c9284bda71c31189482
Source dataset
uspto-grants-2009_06
Patent number
US07550619B2

Reaction notes

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