HCID 18706931, compound → HCID 18706965, compound

HRID 1422118Notes

Reaction equation

HRID 1422118 reaction equation
[CH2:1]([C:3]1[C:4]([C:12]2[CH:22]=[CH:21][C:15]([C:16](OCC)=[O:17])=[CH:14][CH:13]=2)=[CH:5][N:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:1]([C:3]1[C:4]([C:12]2[CH:13]=[CH:14][C:15]([CH2:16][OH:17])=[CH:21][CH:22]=2)=[CH:5][N:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2]

Participants

3

Reactant 2

HCID 18706931HCID 18706931, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18706965HCID 18706965, compoundYield 94%

Procedure

The general synthetic pathway outlined in example 1, step 1-2, have been applied to proper starting materials in the preparation of ethyl 4-(1-ethylindolizine-2-yl)benzoate, which was reduced with lithium aluminium hydride by the general synthetic principles outlined in example 1, step 4, to afford 1-ethyl-2-(4-hydroxymethylphenyl)indolizine in 94% yield. 1H-NMR (CDCl3, 200 MHz) δ: 1.20 (t, 3H); 2.88 (q, 2H); 4.72 (s, 2H); 6.41 (ddd, 1H); 6.61 (ddd, 1H); 7.29-7.52 (m, 6H); 7.83 (d, 1H).

Sources & evidence

ORD record
ord-4fd99c52f0ec4734a92036b5f0d7681d
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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