Dabco → HCID 11508430, compound

HRID 1983583Notes

Reaction equation

HRID 1983583 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)(=[O:4])[CH:2]=[CH2:3].[S:15]1[CH:19]=[CH:18][N:17]=[C:16]1[CH:20]=[O:21].C1N2CCN(CC2)C1>>[OH:21][CH:20]([C:16]1[S:15][CH:19]=[CH:18][N:17]=1)[C:2](=[CH2:3])[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)=[O:4]

Participants

4

Reactant 3

HCID 9237DabcoHCID 27349031,3-Thiazole-2-carbaldehydeHCID 69060682HCID 69060682, compound

Product 1

HCID 11508430HCID 11508430, compoundYield 42%

Procedure

A mixture of 59 mg (0.26 mmol) of 3,4-dichlorophenylmethyl acrylate, 27 mg (0.24 mmol) of 2-thiazolecarboxaldehyde, and 31 mg (0.28 mmol) of DABCO was thoroughly shaken on a Vortex mixer, and then stored at 0° C. overnight. The product was purified by prep HPLC to give 34 mg (0.10 mmol; 42% yield) of the desired Baylis-Hillman adduct, 3,4-dichlorophenylmethyl β-hydroxy-α-methylene-2-thiazolepropanoate. 1H NMR (CDCl3): δ 5.12 (2H), 5.76 (1H), 6.07 (1H), 6.49 (1H), 7.12 (d of d, 1H), 7.71 ppm (d, 1H) MS m/z: 344.0 (M+H).

Workup

  1. customThe product was purified by prep HPLC

Sources & evidence

ORD record
ord-9ea37c5fa74b4a2f9f4f39086ae86385
Source dataset
uspto-grants-2009_06
Patent number
US07541472B2

Reaction notes

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