HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 18446948, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | (-)-2-Butanol | HCID 84682 | — |
| Reactant | 3-Fluoro-4-hydroxybenzaldehyde | HCID 587250 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 18446948 | HCID 18446948 | 12.3% |
Reaction Steps
A solution of 750 mg (5.4 mmol) of 3-fluoro-4-hydroxybenzaldehyde, 403 mg (5.4 mmol) of (R)-(−)-2-butanol and 2 g (7.5 mmol) triphenylphosphine in 10 mL of THF was treated with 1.5 mL of diisopropylazodicarboxylate. The resulting solution was stirred at rt for 14 h, cooled to rt and concentrated. Chromatography on a Biotage 40M cartridge using 4:1 v/v hexanes/Et2O as the eluant afforded 130 mg of the title compound: 1H NMR (500 Mhz) δ 0.99 (t, J=7.6, 3H), 1.35 (d, J=6.2, 3H), 1.58–1.83 (m, 2H), 4.47 (m, 1H), 7.05 (t, J=8.2, 1H), 7.59 (d, J=8.2, 1H), 7.61 (s, 1H), 9.84 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07199142B2 |
| Source dataset | uspto-grants-2007_04 |
| ORD ID | ord-98e32560df2347879b6cdab0ddc7f7d3 |
| Source note | uspto-grants-2007_04 |