(R,Z)-4-(hex-3-enyl)-2,2-dimethyl-1,3-dioxolane → (R,Z)-oct-5-ene-1,2-diol

HRID 1295080Notes

Reaction equation

HRID 1295080 reaction equation
[CH2:1]([C@@H:7]1[CH2:11][O:10]C(C)(C)[O:8]1)[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH3:6]>CC(O)=O>[CH2:11]([OH:10])[C@H:7]([OH:8])[CH2:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH3:6]

Participants

3

Reactant 1

HCID 58906736(R,Z)-4-(hex-3-enyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 58906721(R,Z)-oct-5-ene-1,2-diol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(R,Z)-4-(hex-3-enyl)-2,2-dimethyl-1,3-dioxolane (5.95 g, 32.3 mmol) was stirred in 80% aq. AcOH (50 mL) for 20 h. The mixture was concentrated in vacuo and purified by silica gel chromatography (40% EtOAc in hexanes gradient to 70% EtOAc in hexanes) to give (R,Z)-oct-5-ene-1,2-diol as a clear oil. 1H NMR (400 MHz, CDCl3): δ 5.45 (1H, m), 5.36 (1H, m), 3.75 (1H, m), 3.67 (1H, dd, J=10.8, 2.8 Hz), 3.45 (1H, dd, J=11.2, 7.6 Hz), 2.16 (2H, m), 2.04 (2H, m), 1.50 (2H, m), 0.96 (3H, t, J=7.6 Hz).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by silica gel chromatography (40% EtOAc in hexanes gradient to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a8075bff4a7840eba582a849f9d17283
Source dataset
uspto-grants-2007_07
Patent number
US07241792B2

Reaction notes

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