Ethylene Glycol → 2-(2-Cyclopentyl-1,3-dioxolan-2-yl)acetonitrile

HRID 1917880Notes

Reaction equation

HRID 1917880 reaction equation
[CH:1]1([C:6](=[O:10])[CH2:7][C:8]#[N:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:11](O)[CH2:12][OH:13].Cl[Si](C)(C)C>>[CH:1]1([C:6]2([CH2:7][C:8]#[N:9])[O:13][CH2:12][CH2:11][O:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 135921183-Cyclopentyl-3-oxopropanenitrile

Product 1

HCID 668766282-(2-Cyclopentyl-1,3-dioxolan-2-yl)acetonitrileYield 60%

Procedure

According to the procedure described in Example 133A Step 2, 3-cyclopentyl-3-oxopropanenitrile (2 g, 14 mmol) was added to a mixture of ethylene glycol (2.4 mL, 44 mmol) and chlorotrimethylsilane (5.5 mL, 44 mmol) to give 2-(2-cyclopentyl-1,3-dioxolan-2-yl)acetonitrile (1.5 g, 60%). 1H NMR (300 MHz, CDCl3) δ 4.23-4.15 (m, 2H), 4.12-4.01 (m, 2H), 2.72 (s, 2H), 2.42-2.30 (m, 1H), 1.81-1.45 (m, 8H).

Sources & evidence

ORD record
ord-d5424d605601440c908a8dd05a155150
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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