HCID 19601773, compound → HCID 19601769, compound

HRID 610746Notes

Reaction equation

HRID 610746 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:20](=[O:22])[CH3:21])[CH:8]=[C:9]([C:11](O)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CO.Cl>[C:1]([C:5]1[CH:6]=[C:7]([C:20](=[O:22])[CH3:21])[CH:8]=[C:9]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH2:12])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 19601773HCID 19601773, compound

Product 1

HCID 19601769HCID 19601769, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To 50.0 mg (0.17 mmol) of alcohol 15 in 4 ml of MeOH was added 2 drops of concentrated HCl. The mixture was heated at reflux for 5 min, cooled to RT, quenched with water, and the products extracted with ether. The ether layer was washed (water then brine), dried (MgSO4), filtered and concentrated. Purification by preparative TLC (SiO2, 5% EtOAc-95% hexanes) gave 33.0 mg (0.12 mmol) of 1-[3-t-butyl-5-(1-phenyl-vinyl)-phenyl]-ethanone 16 (71% yield). Rf 0.8; 1H-NMR (CDCl3) δ 1.34 (s, 9H, 3CH3), 2.58 (s, 3H, COCH3), 5.48 (s, 1H,CH=), 5.55 (s, 1H, CH=), 7.34 (m, 5H, Ar--H), 7.56 (t, J=3.7 Hz, 1H, Ar--H), 7.72 (t, J=3.7 Hz, 1H, Ar--H), 7.96 (t, J=3.7 Hz, 1H, Ar--H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 min
  3. customquenched with water
  4. extractionthe products extracted with ether
  5. washThe ether layer was washed (water
  6. dry with materialbrine), dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by preparative TLC (SiO2, 5% EtOAc-95% hexanes)

Sources & evidence

ORD record
ord-4e56cc9e406245b69fe99151cf25817c
Source dataset
uspto-grants-1999_12
Patent number
US05998654

Reaction notes

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