HCID 86761490, compound → HCID 54538906, compound

HRID 1640368Notes

Reaction equation

HRID 1640368 reaction equation
[Si]([O:8][CH:9]([CH:16]([CH3:25])[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:10][CH:11]=[CH:12][C:13]([O-:15])=[O:14])(C(C)(C)C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[OH:8][CH:9]([CH:16]([CH3:25])[CH:17]=[CH:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10][CH:11]=[CH:12][C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 86761490HCID 86761490, compound

Product 1

HCID 54538906HCID 54538906, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
23 °C

Procedure

tert-Butyl (2E, 5S, 6R, 7E)-5-[(tert-butyl-dimethylsilyl)-oxy]-6-methyl-8-phenyl-octa-2,7-dienoate (725 mg, 1.74 mmol) was dissolved in CH2Cl2 (8 mL) and trifluoroacetic acid (2 mL). The solution was stirred at 23° C. for 4 h then concentrated in-vacuo. Residual trifluoroacetic acid was removed by coevaporation with toluene. Flash chromatography (2% MeOH/CH2Cl2+1% AcOH) afforded the title compound 9 (210 mg, 49%) as pale yellow oil. TLC Rf=0.24 (2% MeOH/CH2Cl2+1% AcOH, KMnO4 stain); 1H NMR (CDCl3, 400 MHz) δ 7.23-7.39 (m, 5H), 7.16 (dt, J=15.6, 7.4, 1H), 6.49 (d, J=15.8, 1H), 6.13 (dd, J=15.8, 8.7, 1H), 5.94 (dt, J=15.6, 1.4, 1H), 3.68 (ddd, J=7.9, 6.0, 3.9, 1H), 2.50-2.56 (m, 1H), 2.36-2.44 (m, 2H), 1.16 (d, J=6.8, 3H); 13C NMR (CDCl3, 101 MHz) δ 171.0, 148.5, 137.0, 132.4, 130.9, 128.8, 127.7, 126.4, 122.9, 73.9, 43.6, 37.5, 17.0; MS (ESI+) m/z 269.1 [M+Na]+ (C15H18NaO3 requires 269.1).

Workup

  1. concentrationthen concentrated in-vacuo
  2. customResidual trifluoroacetic acid was removed by coevaporation with toluene

Sources & evidence

ORD record
ord-c8ec5234e2ed43bc96b6843ea2316d37
Source dataset
uspto-grants-2012_02
Patent number
US08114640B2

Reaction notes

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