1,2-Dichloroethane → Butanal

HRID 638338Notes

Reaction equation

HRID 638338 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:26](=[O:27])[N:12]2[C:13]([C:20]([O:22]CC=C)=[O:21])=[C:14]([N:17]=[N+]=[N-])[CH2:15][S:16][C@H:11]12)=[O:8].Cl[CH2:29][CH2:30]Cl>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:26](=[O:27])[N:12]2[C:13]([C:20]([OH:22])=[O:21])=[C:14]([N:17]=[C:7]([N:9]3[CH2:30][CH2:29][O:27][CH2:26][CH2:10]3)[CH2:6][CH2:2][CH3:3])[CH2:15][S:16][C@H:11]12)=[O:8].[CH:7](=[O:8])[CH2:6][CH2:2][CH3:3].[NH:12]1[CH2:13][CH2:20][O:22][CH2:10][CH2:26]1

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 131714474HCID 131714474, compound

Product 3

HCID 261ButanalHCID 8083MorpholineHCID 70478177HCID 70478177, compound

Procedure

To a solution of 1.8 g. of allyl 7β-(2-thienylacetylamino)-3-azido-3-cephem-4-carboxylate in about 100 ml. of 1,2-dichloroethane was added 0.628 g. (1 equiv.) of the enamine formed with n-butyraldehyde and morpholine and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was evaporated to dryness at 40° C. and the residue chromatographed on silica gel using 10% ethyl acetate in toluene vs. ethyl acetate. Multiple fractions were collected and the fractions containing the product (via tlc) were pooled and evaporated to yield 1.479 g (72.5% yield) of allyl 7β-(2-thienylacetylamino)-3-[1-(4-morpholinyl)butylideneamino]-3-cephem-4-carboxylate.

Sources & evidence

ORD record
ord-24309540f3de407eb3774bba4f1e28df
Source dataset
uspto-grants-1985_12
Patent number
US04560749

Reaction notes

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