Hydrochloric Acid → HCID 5368428, compound

HRID 1497011Notes

Reaction equation

HRID 1497011 reaction equation
[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[C:11](OCC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C.Cl>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14487Diisobutylaluminum hydride2×HCID 5368479HCID 5368479, compound

Product 1

HCID 5368428HCID 5368428, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (E)-ethyl 5-phenylpent-2-enoate (732 mg) in dry toluene (5 ml) was cooled to −78° C. DIBAL-H (1 M in hexanes, 7.17 ml) was added dropwise and the mixture was stirred for 3 h. A second portion of DIBAL-H (1 M in hexanes, 0.717 ml) was added and stirring was continued for another 3 h. The mixture was allowed to warm-up to RT and hydrolyzed with 1 M aqueous HCl (5 ml). Additional 3M aqueous HCl was added until pH=1 and the aqueous layer was extracted with EtOAc (3×). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was dissolved in dichloromethane (5 ml) and TEMPO (28.0 mg), potassium bromide (42.6 mg) and water (5 ml) were added. Aqueous sodium hypochlorite solution (13%, 1.642 ml) was added dropwise. The mixture was stirred at room temperature for 15 h. After phase separation the aqueous layer was extracted with CH2Cl2. The combined organic layer was washed with 1 M HCl, water and brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography to yield a slightly orange oil.

Workup

  1. stirringstirring
  2. waitwas continued for another 3 h
  3. extractionthe aqueous layer was extracted with EtOAc (3×)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. dissolutionThe crude product was dissolved in dichloromethane (5 ml)
  8. additionTEMPO (28.0 mg), potassium bromide (42.6 mg) and water (5 ml) were added
  9. additionAqueous sodium hypochlorite solution (13%, 1.642 ml) was added dropwise
  10. stirringThe mixture was stirred at room temperature for 15 h
  11. customAfter phase separation the aqueous layer
  12. extractionwas extracted with CH2Cl2
  13. washThe combined organic layer was washed with 1 M HCl, water and brine
  14. dry with materialdried over Na2SO4
  15. concentrationconcentrated
  16. customThe crude product was purified by flash column chromatography
  17. customto yield a slightly orange oil

Sources & evidence

ORD record
ord-f2267369b5f8428f9a09d9cb54f5d2d1
Source dataset
uspto-grants-2015_12
Patent number
US09199948B2

Reaction notes

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