Bis(2-bromoethyl) ether → 4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 1868661Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#[N:13])=[CH:7][CH:6]=1.Br[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Br>CN1C(=O)CCC1.CCOCC>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2([C:12]#[N:13])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of NaH (3.1 g, 76 mmol) in 100 mL NMP stirred at 0° C., was treated dropwise with the mixture of 2-(4-methoxyphenyl)acetonitrile (4.5 g, 31 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (7.1 g, 31 mmol) in 30 mL ether. The mixture was allowed to warm to room temperature and stirred for 5 hours, M+Na=240. The mixture was carefully quenched with 100 mL H2O, and the pH was adjusted to 5. The mixture was extracted with ether (3×100 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (20 mL). The organic layer was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10-20% EtOAc/hexane to give 5.2 g of the product as a pale yellow oil. MS (m/z)=240 (M+H)+.

Workup

temperatureto warm to room temperature
stirringstirred for 5 hours
customThe mixture was carefully quenched with 100 mL H2O
extractionThe mixture was extracted with ether (3×100 mL)
washThe combined organic layers were washed with H2O (3×50 mL) and brine (20 mL)
dry with materialThe organic layer was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
custompurified by column chromatography
washeluting with 10-20% EtOAc/hexane

Sources & evidence

ORD record: ord-e8d69cdcbb4b4108b8d51f6bf5a83f69
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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