Tetrahydrofuran → HCID 69587403, compound

HRID 967992Notes

Reaction equation

[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[CH:24]=[O:25])[CH2:4][CH3:5])[CH3:2].[Li].[CH2:27]1COCC1>>[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=2[CH3:21])[C:8]=1[CH:24]([OH:25])[CH3:27])[CH2:4][CH3:5])[CH3:2]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 3028194Lithium

HCID 86584322HCID 86584322, compound

Product 1

HCID 69587403HCID 69587403, compound

Procedure

The title compound was prepared by reacting 4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3-carbaldehyde with methylithium lithium in THF at −78° C. The desired product was isolated after silica gel column chromatography to give 60.1% of colorless oil. 1H NMR(CDCl3) d 6.87(s, 2H), 6.06(s, 1H), 5.7(q, 1H), 3.3(m, 1H), 2.29(s, 3H), 2.12(s, 6H), 2.069s, 3H), 1.4-1.7(m, 4H), 1.59(d, 3H), 0.8-1.0(m, 6H) ppm.

Workup

customThe title compound was prepared
customat −78° C

Sources & evidence

ORD record: ord-077f5be3b2c94e2d82d2915166fa2ccf
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956047B1

Reaction notes

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