HCID 69069452, compound → HCID 69061805, compound

HRID 1295087Notes

Reaction equation

HRID 1295087 reaction equation
[CH:1]1([CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]2[CH2:13][O:12]C(C)(C)[O:10]2)[CH2:3][CH2:2]1>CC(O)=O>[CH:1]1([CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]([OH:10])[CH2:13][OH:12])[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 69069452HCID 69069452, compound

Product 1

HCID 69061805HCID 69061805, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Stirred 4-(5-Cyclopropyl-pent-3-enyl)-2,2-dimethyl-[1,3]dioxolane (0.30 g, 1.4 mmol) in 80% AcOH (5 mL) overnight at room temperature. Concentrated and purified by silica gel chromatography (70˜90% EtOAc in hexanes) to collect 7-Cyclopropyl-hept-5-ene-1,2-diol as a clear oil. 1H NMR (400 MHz, CDCl3): δ 5.52–5.47 (m, 1H), 5.41–5.35 (m, 1H), 3.77–3.71 (m, 1H), 3.66 (d, 1H, J=11.2 Hz), 3.46 (dd, 1H, J1=11.2 Hz, J2=7.7 Hz), 2.19–2.10 (m, 2H), 1.97 (t, 2H, J=7.1 Hz), 1.53–1.46 (m, 2H), 0.74–0.68 (m, 1H), 0.44–0.39 (m, 2H), 0.08–0.04(m, 2H).

Workup

  1. concentrationConcentrated
  2. custompurified by silica gel chromatography (70˜90% EtOAc in hexanes)
  3. customto collect 7-Cyclopropyl-hept-5-ene-1,2-diol as a clear oil

Sources & evidence

ORD record
ord-0adba13d7e6b4744bd5d326a121acf49
Source dataset
uspto-grants-2007_07
Patent number
US07241792B2

Reaction notes

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