Bis(2-bromoethyl) ether → methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate

HRID 2391148Notes

Reaction equation

HRID 2391148 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:2].[H-].[Na+].Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br>CS(C)=O>[C:1]([C:3]1([C:4]2[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)#[N:2]

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 10821136Methyl 3-(cyanomethyl)benzoate

Product 1

HCID 57441036methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoateYield 46.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Using methyl 3-(cyanomethyl)benzoate (1.0 g, 5.7 mmol), sodium hydride (60% in oil, 0.69 g, 17 mmol), bis(2-bromoethyl)ether (1.8 g, 6.9 mmol) and dimethyl sulfoxide (12 mL) as starting materials and in the same manner as in Reference Example 31, the title compound (650 mg, 46%) was obtained as a colorless oil.

Sources & evidence

ORD record
ord-ae7bf08fa58142d5a40cc0e18ce7882f
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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