Dabco → HCID 11688627, compound

HRID 1983582Notes

Reaction equation

HRID 1983582 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)(=[O:4])[CH:2]=[CH2:3].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[O:24])[CH:18]=1.N12CCN(CC1)CC2>>[OH:24][CH:23]([C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1)[C:2](=[CH2:3])[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:15])[F:16])[CH:8]=1)=[O:4]

Participants

4

Reactant 3

HCID 9237DabcoHCID 103713-PyridinecarboxaldehydeHCID 2777443HCID 2777443, compound

Product 1

HCID 11688627HCID 11688627, compoundYield 52%

Procedure

A mixture of 62 mg (0.27 mmol) of 3-(trifluoromethyl)phenylmethyl acrylate, 29 mg (0.27 mmol) of pyridine-3-carboxaldehyde, and 30 mg (0.27 mmol) of 1,4-diazabicyclo [2.2.2]octane (DABCO) was thoroughly shaken on a Vortex mixer, and then stored at 0° C. overnight. The product was purified by preparative HPLC (prep HPLC) using a Gilson 210 HPLC/fraction handler to give 47 mg (0.14 mmol; 52% yield) of the desired Baylis-Hillman adduct, 3-(trifluoromethyl)phenylmethyl β-hydroxy-α-methylene-3-pyridinepropanoate. 1H NMR (CDCl3): δ 5.18 (s, 2H), 5.63 (1H), 5.98 (1H), 6.45 (1H), 7.70 (d of t, 1H), 8.49 (d of d, 1H), and 8.56 ppm (d, 1H). MS m/z: 338.1 (M+H).

Workup

  1. customThe product was purified by preparative HPLC (prep HPLC)

Sources & evidence

ORD record
ord-0263ac97429643eeb65f54a64d33c62d
Source dataset
uspto-grants-2009_06
Patent number
US07541472B2

Reaction notes

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