Dichloromethane → HCID 86755128, compound

HRID 377380Notes

Reaction equation

HRID 377380 reaction equation
[CH2:1]1[CH2:11][CH2:10][N:9]2C(=NCCC2)C[CH2:2]1.N1C2C(=CC=CC=2)C=CC=1/C=C/[CH:24]=[O:25].[CH3:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C[CH2:34][O:35][C:36]([CH3:38])=[O:37].[CH2:39](Cl)Cl>>[N:9]1[C:10]2[C:31](=[CH:32][CH:2]=[CH:1][CH:11]=2)[CH:30]=[CH:29][C:28]=1/[CH:27]=[CH:26]/[CH:39]=[C:38](\[O:25][CH3:24])/[C:36]([O:35][CH3:34])=[O:37]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6479252HCID 6479252, compoundHCID 21899848Ethylacetate heptane

Product 1

HCID 86755128HCID 86755128, compoundYield 66.6%

Procedure

A suspension of methyl 2-methoxy-2-triphenylphosphonium acetate (2.22 g, 5.0 mmol) and DBU (750 mg, 5.0 mmol) in CH2Cl2 (20 ml) was stirred at RT for 15 minutes. Then (2E)-3-(quinolin-2-yl)-propenal (460 mg, 2.51 mmol) was added and the reaction conducted as seen for example 1. After a chromatography on silicagel (n-heptane/EtOAc 4/1) pure title compound was obtained (450 mg, 1.67 mmol, yield 66.6%) as brown crystals, m.p.=88°.

Sources & evidence

ORD record
ord-165cd2eace9648348de9b6795c5eec39
Source dataset
uspto-grants-2000_02
Patent number
US06025390

Reaction notes

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