Water → 6-Octyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1921684Notes

Reaction equation

HRID 1921684 reaction equation
B1[CH:6]2[CH2:7][CH2:8][CH2:9][CH:2]1[CH2:3][CH2:4][CH2:5]2.C=CCCCCCC.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[K+].[Br-].O.[O:29]=[C:30]1[CH2:39][CH2:38][CH2:37][C:36]2[CH:35]=[C:34](OS(C(F)(F)F)(=O)=O)[CH:33]=[CH:32][C:31]1=2>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:8]([C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][CH:33]=1)[C:30](=[O:29])[CH2:39][CH2:38][CH2:37]2)[CH2:9][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

8

Reactant 6

HCID 962WaterHCID 81251-OcteneHCID 62657Potassium Phosphate, TribasicHCID 789669-Borabicyclo(3.3.1)nonaneHCID 253877Potassium BromideHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 575773736-Octyl-3,4-dihydronaphthalen-1(2H)-oneYield 82%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

9-BBN (0.5 M solution in THF, 20.2 mL, 10.1 mmol) was added to 1-octene (1.6 mL, 10.1 mmol) at room temperature. The solution was stirred, at room temperature, overnight. After this time, K3PO4 (2.93 g, 13.8 mmol), Pd(Ph3P)4 (191 mg, 0.17 mmol, 1.8 mol %), KBr (1.2 g, 10.1 mmol) and degassed H2O (0.18 mL, 10 mmol) were added. This was followed by a solution of compound 2 (2.7 g, 9.2 mmol) in dry degassed THF (10 mL). The reaction mixture was heated at 65° C. under argon for 2 hours. After cooling, the solution was acidified to pH 1 and extracted into EtOAc (100 mL). The aqueous layer was re-extracted with EtOAc (50 mL) and the combined organics washed with H2O (20 mL) and brine (40 mL). The organic layer was dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, 5% EtOAc in hexanes) to provide 1.93 g of compound 3 (82%).

Workup

  1. additionwere added
  2. customin dry
  3. customdegassed THF (10 mL)
  4. temperatureThe reaction mixture was heated at 65° C. under argon for 2 hours
  5. temperatureAfter cooling
  6. extractionextracted into EtOAc (100 mL)
  7. extractionThe aqueous layer was re-extracted with EtOAc (50 mL)
  8. washthe combined organics washed with H2O (20 mL) and brine (40 mL)
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated under vacuum
  11. customThe residue was purified by column chromatography (Silica gel, 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b44b29c654214bfa97b93bef5371a170
Source dataset
uspto-grants-2012_05
Patent number
US08173710B2

Reaction notes

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