4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridine → HCID 67077239, compound

HRID 1959613Notes

Reaction equation

HRID 1959613 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]([Cl:16])[CH:5]=[CH:4][N:3]=1.CC1C=CN=C(C=C)C=1[CH2:26][O:27]C1CCCCO1.CC1C=CN=C(CO)C=1COC1CCCCO1>[Pd]>[Cl:16][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH2:26][OH:27])[C:7]=1[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1

Participants

5

Reactant 3

HCID 441905854-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridineHCID 44191034[4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-methanolHCID 86645362HCID 86645362, compound

Product 1

HCID 67077239HCID 67077239, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Pd catalyzed vinylation of 2,4-dichloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine (1.71 g. 6.52 mmol) according to the synthesis of 4-methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridine subsequent ozonolysis and reduction according to the synthesis of [4-methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-methanol and flash chromatographic purification yielded the title compound. MS (m/z): 257.8 [M+H+].

Workup

  1. custompurification

Sources & evidence

ORD record
ord-fc1a5bcb582240d8ae7531fe511d11ba
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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