3-Butene-1,2-diol → 1,2,5,6-Hexanetetrol

Self-metathesis of 1,2-dihydroxy-3-butene. 1,2-Dihydroxy-3-butene (158 mg, 1.8 mmol) and (PCy3)2Cl2Ru═CHPh (30 mg, 0.036 mmol, 2.0 mol %) were dissolved in dry dichloromethane (5 ml). The solution was degassed then heated to reflux. Gradually, the solution's purple color changed to red-brown and a white solid formed. After 21 h heating was stopped and the white solid was filtered and dried in vacuo to give 11 mg, (0.074 mmol, 8.2% yield) of 3,4-dideoxyhexitol. 1H NMR (D2O) δ 5.80 (s, 1H), 4.25 (br s, 1H), 3.62 (m, 1H), 3.52 (m, 1H).

1. customThe solution was degassed
2. temperaturethen heated to reflux
3. customformed
4. temperatureAfter 21 h heating
5. filtrationthe white solid was filtered
6. customdried in vacuo

ORD record

ord-c349f55301364a24bc65e4314dabb9f4

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07002049B2