Sulfuric Acid → Pyridin-2-yl(2-m-tolyltetrahydrofuran-2-yl)methanone

HRID 1620993Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[C:13]1([CH3:26])[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2([C:24]#N)[CH2:23][CH2:22][CH2:21][O:20]2)[CH:14]=1.[OH:27]S(O)(=O)=O>C1COCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:24]([C:19]1([C:15]2[CH:14]=[C:13]([CH3:26])[CH:18]=[CH:17][CH:16]=2)[CH2:23][CH2:22][CH2:21][O:20]1)=[O:27]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-bromopyridine (418 mg, 2.65 mmol) in THF (10 mL) was added n-BuLi (1.65 mL, 2.65 mmol, 1.6 N in hexane) at −78° C. After 15 mins, a solution of Example 91C (4.45 mg, 1.76 mmol) in THF (2 mL) was added. The mixture was stirred at −78° C. for 15 minutes and 2 mL of 1 M H2SO4 was added slowly. Then the mixture was heated at 50° C.-60° C. for 30 minutes. After cooling to room temperature, the aqueous phase was separated and extracted with ethyl acetate (15 mL×3). The combined organic phases was washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to provide the title compound. LC-MS: m/z (M+H): 268.

Workup

temperatureThen the mixture was heated at 50° C.-60° C. for 30 minutes
temperatureAfter cooling to room temperature
customthe aqueous phase was separated
extractionextracted with ethyl acetate (15 mL×3)
washThe combined organic phases was washed with water (50 mL) and brine (50 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-dc08563a0ca14bebb1570fae1d79f629
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772500B2

Reaction notes

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