1,3-Dioxolane, 2-(bromomethyl)- → HCID 68821812, compound

HRID 733439Notes

Reaction equation

HRID 733439 reaction equation
Br[CH2:2][CH:3]1[O:7][CH2:6][CH2:5][O:4]1.[CH:8]1([C:17]#[N:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[O:4]1[CH2:5][CH2:6][O:7][CH:3]1[CH2:2][C:8]1([C:17]#[N:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 2733832Lithium HexamethyldisilazideHCID 30152772,3-Dihydro-1H-indene-1-carbonitrile

Product 1

HCID 68821812HCID 68821812, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-bromomethyl-1,3-dioxolane (12.94 ml, 125.0 mmole) was added to a solution of 1-indanecarbonitrile (16.27 g, 113.6 mmole) in 100 ml of THF and cooled to 0° C. After the dropwise addition of 1M LHMDS (125 ml) the solution was stirred at 0° C. for 20 min then at room temperature for 20 min. After the removal of solvent the residue was flashed of silica using 15% EtOAc and Hexanes to afford 19.23 g of 1-(1,3-dioxolan-2-ylmethyl)-1-indanecarbonitrile (74% yield) as a thick oil.

Workup

  1. waitat room temperature for 20 min
  2. customAfter the removal of solvent the residue

Sources & evidence

ORD record
ord-46657b17b78c4458a39adbecd34ffc07
Source dataset
uspto-grants-2009_09
Patent number
US07589204B2

Reaction notes

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