Water → HCID 57908775, compound

HRID 606549Notes

Reaction equation

HRID 606549 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.[CH:29]1[C:34]2[CH2:35][CH2:36][CH2:37][CH2:38][C:39](=[O:40])[C:33]=2[CH:32]=[CH:31][C:30]=1OS(C(F)(F)F)(=O)=O>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:30]1[CH:31]=[CH:32][C:33]2[C:39](=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][C:34]=2[CH:29]=1)[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 57908774HCID 57908774, compound

Product 1

HCID 57908775HCID 57908775, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

(7-octyl-1-benzosuberone). 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 rt. The solution was then 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 followed by a solution of 2 (2.7 g, 9.2 mmol) in dry degassed THF (10 mL). The reaction mixture was then heated to 65° C. under argon for 2 h. 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 give 1.45 g compound 3 (72%). 1H NMR (300 MHz, CDCl3) δ 0.85 (t, 3H, J=6.95 Hz), 1.24 (bs, 10H), 1.58 (p, 2H, J=6.95 Hz), 2.06 (m, 4H, J=5.85 Hz), 2.57 (t, 4H, J=6.95 Hz), 2.87 (t, 2H, J=6.22 Hz), 7.01 (s, 1H), 7.06 (d, 1H, J=8.05 Hz), 7.91 (d, 1H, J=8.06 Hz).

Workup

  1. additionwere added
  2. customin dry
  3. customdegassed THF (10 mL)
  4. temperatureThe reaction mixture was then heated to 65° C. under argon for 2 h
  5. temperatureAfter cooling the solution
  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-1996ad24d10444008495877d6691da67
Source dataset
uspto-grants-2011_03
Patent number
US07915315B2

Reaction notes

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