Acetone → HCID 54261900, compound

HRID 265245Notes

Reaction equation

HRID 265245 reaction equation
[C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1/[CH:20]=[CH:21]/[P:22](=[O:29])([O:26]CC)[O:23]CC)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].Br[Si](C)(C)C.CC(C)=O.O>C(Cl)Cl.[2H]C([2H])(Cl)Cl>[C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[CH:21][P:22](=[O:23])([OH:29])[OH:26])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 962Water2×HCID 76113Bromotrimethylsilane2×HCID 19033961HCID 19033961, compound

Product 1

HCID 54261900HCID 54261900, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 131719048HCID 131719048, compoundSolvent

Procedure

Diethyl E-2-[2-(1-tridecynyl)phenyl]ethenylphosphonate (0.521 g, 1.25 mmol) prepared according to Example 13 was dissolved in CH2Cl2 : CD2Cl2 (1:1, 9 ml ) and stirred while bromotrimethylsilane (0.38 g, 2.48 mmol) was added. The reaction was monitored by 1H and 31P NMR. Additional bromotrimethylsilane (0.1 ml, 0.76 mmol) was added after 6.5 hours. After stirring for 30 hours, the solvent was removed under reduced pressure. Acetone (5 ml) was added, along with water (0.15 ml, 8.3 mmol). The reaction mixture was stirred for about 42 hours, then stripped. NMR indicated that the reaction was incomplete. Acetone (3 ml) and water (0.2 ml, 11.1 mmol) were added back and the reaction was stirred overnight. The solvent was then removed, and the residue was recrystallized from heptane, as a white crystalline solid, 0.348 g, 0.96 mmol, 76.8% yield; mp 82°-83° C.; 1H NMR (CDCl3) ∂0.85 (t, J=6.7 Hz, 3H), 1.10 to 1.45 (m, 16H), 1.59 (m, 2H), 2.43 (t, J=7.1 Hz, 2H), 6.44 (t, J=18.5 Hz, 1H), 7.26 (m, 2H), 7.41 (m, 1H), 7.54 (m, 1H), 8.04 (dd, J=24.2, 17.6 Hz, 1H), 10.46 (br s, 2H); FAB mass spectrum m/z 363 (M+H)+.

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. stirringThe reaction mixture was stirred for about 42 hours
  4. stirringthe reaction was stirred overnight
  5. customThe solvent was then removed
  6. customthe residue was recrystallized from heptane, as a white crystalline solid, 0.348 g, 0.96 mmol, 76.8% yield

Sources & evidence

ORD record
ord-8bb2a1ae58c240cc8c98b17ef4cfe4ed
Source dataset
uspto-grants-1997_07
Patent number
US05648349

Reaction notes

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