CID 406 → HCID 72237317, compound

HRID 1952425Notes

Reaction equation

HRID 1952425 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].[C:21](Cl)(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.P(=O)([O-])[O-]>C(Cl)Cl>[C:21]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][P:13]([O:14][CH2:15][CH3:16])([O:17][CH2:18][CH3:19])=[O:20])(=[O:30])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 406CID 406HCID 660233-Phenylprop-2-enoyl chlorideHCID 45158972Diethyl (11-hydroxyundecyl)phosphonate

Product 1

HCID 72237317HCID 72237317, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The diethyl 11-hydroxyundecylphosphonate (1.00 g, 3.24 mmol) was combined with TEA (0.48 mL, 3.40 mmol) in 15 mL dry DCM in a 50 mL round-bottomed flask (rbf) and the mixture was brought down to 0° C. Cinnamoyl chloride (566 mg, 3.40 mmol) was added dropwise. The reaction was stirred for 2 hours and then stopped once most of the starting phosphonate was consumed. TLC in ethyl acetate showed several new spots. The reaction mixture was then washed 3× (20 mL) NaOH followed by sodium thiosulfate and water washes. The organic layer was then dried over magnesium sulfate and the solvent removed. A chromatography column in ethyl acetate was run and the desired product was isolated as a yellow-tinted oil with Rf=0.60 (580 mg, 41% yield). 1H NMR (400.13 MHz, CDCl3) δ 7.68 (d, J=16.02 Hz), 7.53 (m, 2H), 7.38 (m, 3H), 6.44 (d, J=16.02 Hz), 4.20 (t, J=6.74 Hz, 2H), 4.08 (m, 4H), 1.79-1.49 (m, 6H), 1.43-1.22 (m, 20H). 13C{1H} NMR (100.61 MHz, CDCl3) δ 167.02, 144.48, 134.39, 130.14, 128.79 (2C), 127.97 (2C), 118.21, 64.65, 61.28 (d, J=6.54 Hz, 2C), 30.54 (d, J=16.94), 29.42 (2C), 29.28, 29.20, 29.02, 28.65, 25.90, 25.62 (d, J=140.40 Hz), 22.33 (d, J=5.21 Hz), 16.42 (d, J=5.92 Hz, 2C). 31P{1H} NMR (161.98 MHz, CDCl3): δ 33.32. Analysis found (calculated) %: C, 65.39 (65.73); H, 9.05 (8.96). MS (ESI, m/z): 439 ([M+H]+, 100%). Exact mass found (calculated for [M+H]+, m/z): 439.25720 (439.26079).

Workup

  1. customwas brought down to 0° C
  2. customwas consumed
  3. washThe reaction mixture was then washed 3× (20 mL) NaOH
  4. dry with materialThe organic layer was then dried over magnesium sulfate
  5. customthe solvent removed

Sources & evidence

ORD record
ord-1e99f40230d1481fa7f8b0fa3de2bc8d
Source dataset
uspto-grants-2013_03
Patent number
US08405069B2

Reaction notes

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