Ethanol → HCID 58691167, compound

HRID 1392106Notes

Reaction equation

HRID 1392106 reaction equation
C(=O)(O[CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)OC.[C:15]1([C@@H:21]([N:23]([C@H](C2C=CC=CC=2)C)P2OC3C=CC4C=CC=CC=4C=3C3C4C(C=CC=3O2)=CC=CC=4)C)[CH:20]=CC=C[CH:16]=1.CCO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir]>[CH2:21]([NH:23][C@H:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:6]=[CH2:5])[CH:15]([CH3:20])[CH3:16]

Participants

7

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 10035469HCID 10035469, compoundHCID 11731247N,N-Bis((S)-1-phenylethyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine

Product 1

HCID 58691167HCID 58691167, compound

Reagents, catalysts & solvents 2

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimerCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Methyl (2E)-3-phenylprop-2-en-1-yl carbonate (1.5 g) in THF (25 ml), was added N,N-bis[(1S)-1-phenylethyl]dinaphtho[1,2-f:2′,1′-d][1,3,2]dioxaphosphepin-4-amine (420 mg), and chloro(1,5-cyclooctadiene)iridium(I) dimer (105 mg) at RT under N2. The mixture was heated at reflux overnight. Evaporated material then redissoled in a 50:50 mixture of EtOH:THF. To this solution was added macro porous p-toluenesulfonic acid resin (10 g) and the mixture was gently agitated for 3 h. At this time the resin was washed completely with THF, THF:EtOH and EtOH. To a suspension of the resin in MeOH (75 ml) was added 7 N NH3.MeOH (75 ml). This mixture was gently agitated for 2 hours and filered, washing with MeOH, THF, THF:MeOH, and DCM. Evaporating this filtrate left a yellow oil (1.2 g). This oil was then distilled on a kuglerohr vacumme distilation aparatus. This left the title compound as a clear oil. (830 mg, 53%). 1H NMR (300 MHz, CDCl3) δ 0.90 (d, 6H, J=6.6 Hz), 1.64-1.81 (m, 1H), 2.18-2.45 (m, 2H), 4.15 (d, 1H, J=6.9 Hz), 5.06-5.22 (m, 2H), 5.85-5.97 (m, 1H), 7.20-7.41 (m, 5H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. washAt this time the resin was washed completely with THF, THF
  4. additionTo a suspension of the resin in MeOH (75 ml)
  5. additionwas added 7 N NH3
  6. stirringThis mixture was gently agitated for 2 hours
  7. washwashing with MeOH, THF, THF
  8. customEvaporating this filtrate
  9. waitleft a yellow oil (1.2 g)
  10. distillationThis oil was then distilled on a kuglerohr vacumme distilation aparatus
  11. waitThis left the title compound as a clear oil

Sources & evidence

ORD record
ord-b705621faf0243d884fc75100195657f
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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