1,2-Dimethoxyethane → 4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridine

HRID 1959603Notes

Reaction equation

Cl[C:2]1[C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:6]([CH3:16])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].CO[CH2:25][CH2:26]OC>O.[Pd]>[CH3:16][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH:25]=[CH2:26])[C:7]=1[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-4-methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine (500 mg. 2.07 mmol) was dissolved in a mixture of 1,2-dimethoxyethane (16.5 mL) and water (7 mL). K2CO3 (286 mg. 2.07 mmol) and 2,4,6-trivinyl-cyclotriboroxane pyridine complex (498 mg. 2.07 mmol) were added and the reaction mixture was degassed two times before the addition of Pd((PPh3)4 (120 mg. 0.10 mmol). The reaction mixture was stirred at 100° C. for 18 h. The solvents were removed in vacuo and the residue was purified by flash chromatography on silica gel (elution with hexane/EtOAc 6:1) to give the title compound. MS (m/z): 234.1 [M+H+]

Workup

customthe reaction mixture was degassed two times
customThe solvents were removed in vacuo
customthe residue was purified by flash chromatography on silica gel (elution with hexane/EtOAc 6:1)

Sources & evidence

ORD record: ord-ecf74380dd4e4471a5c7693d02b4cff4
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410134B2

Reaction notes

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