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Tetrahedron Letters

Volumn 36, Issue 51, 1995, Pages 9253-9256

Solid phase synthesis of alkenes using the horner-wadsworth-emmons reaction and monitoring by gel phase 31P NMR

(2) Johnson, Charles R a Zhang, Birong a

a Arris Pharmaceutical Corporation (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0028850172 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(95)02017-J Document Type: Article

Times cited : (85)

References (20)

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- 31P NMR shows only a resonance at δ 0 ppm. The resin was washed with water, DMF, methanol and dried. Cleavage from the resin was with 2 ml of TFA / water (95/5) for 1 h The solution was conc, and dried under vacuum. [[Truncated]]

14
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- 4. A sample of about 50 mg of resin in a regular 5mm NMR tube was used. Addition of about 25% deuterated solvent was adequate for a lock signal. The spectra were acquired at 122 MHz and a recycle time of 1.3 seconds. Spectra with adequate signal to noise ratios required a few hundred acquisitions, but less than 10 minutes of spectrometer time.

15
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- 2O solution. Addition of TEA and lithium bromide to the resin 5 in acetonitrile without aldehyde results in complete conversion to the material with the P resonace at δ 17.6. However, neither the amide linked phosphonate 1 nor trielhylphosphonoacelate show rapid ester cleavage under the same [[Truncated]]

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