2-(2-Bromoethyl)-1,3-dioxolane → HCID 68818475, compound

HRID 733440Notes

Reaction equation

HRID 733440 reaction equation
Br[CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.[CH:9]1([C:18]#[N:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[O:5]1[CH2:6][CH2:7][O:8][CH:4]1[CH2:3][CH2:2][C:9]1([C:18]#[N:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 2733832Lithium HexamethyldisilazideHCID 30152772,3-Dihydro-1H-indene-1-carbonitrile

Product 1

HCID 68818475HCID 68818475, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2(2-bromoethyl)-1,3-dioxolane (14.09 ml, 120.1 mmole) was added to a solution of 1-indanecarbonitrile (15.63 g, 109.2 mmole) in 100 ml of THF and cooled to 0° C. After the dropwise addition of 1M LHMDS (120 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 1-[2-(1,3-dioxolan-2-yl)ethyl]-1-indanecarbonitrile 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-79a6e637825f4880bd9a1b42af2b2b27
Source dataset
uspto-grants-2009_09
Patent number
US07589204B2

Reaction notes

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