Hexane → HCID 86608637, compound

HRID 646524Notes

Reaction equation

HRID 646524 reaction equation
[Br-].[C:2]1([PH+:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH2:22]CCC.CCCCCC.[C:32]([O:40][C:41]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][C:42]=1[C:43]([O:45]C)=O)(=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[CH2:32]([O:40][C:41]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][C:42]=1[C:43](=[O:45])[CH:22]=[P:8]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 517696Phosphine, triphenyl-, hydrobromideHCID 40567378HCID 40567378, compoundHCID 178418339Butyllithium

Product 1

HCID 86608637HCID 86608637, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of triphenylphosphonium bromide (2.14 g, 6.0 mmol) in dried THF (30 ml) at room temperature was added 1.6M n-BuLi in hexane (5.25 ml, 8.39 mmol). The orange suspension was stirred for 3 hours. Next, a solution of methyl 2-benzoyloxy-5-chloro-benzoate (0.83 g, 3.0 mmol) in THF (8 ml) was slowly added. The resulting mixture was stirred at 60° C. for 2 hours and filtered after cooled. DCM (100 ml) was added to the filtrate and the combined organic layers were washed with brine (2×80 ml). After filtration and evaporation of the solvent, yellow oil was obtained (2.0 g). They were then purified by chromatography, eluted with EtOAc:hexane/1:1, yielded 0.97 g solids. Rf=0.43. 1H NMR (d6-acetone) δ=7.80-7.52 (20H, m); 7.40-7.20 (1H+1H+1H, m); 5.25 (2H, s); 4.72 (1H, s, trans-H) and 4.62 (1H, s, cis-H). LCMS: (M+1)+=521.2 (RT=5.94 min.)

Workup

  1. stirringThe resulting mixture was stirred at 60° C. for 2 hours
  2. filtrationfiltered
  3. temperatureafter cooled
  4. additionDCM (100 ml) was added to the filtrate
  5. washthe combined organic layers were washed with brine (2×80 ml)
  6. filtrationAfter filtration and evaporation of the solvent
  7. customyellow oil was obtained (2.0 g)
  8. customThey were then purified by chromatography
  9. washeluted with EtOAc

Sources & evidence

ORD record
ord-adacce1ec0034a8091cb49c1b5476caa
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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