Dicyclohexylcarbodiimide → 4,4-di(1-Hexyl)-1,2-dihydro-7-methyl-9-[4-(pyrrolidino) butyryloxy]-4H-thieno[2,3-c][1]benzopyran hydrobromide

HRID 1657648Notes

Reaction equation

HRID 1657648 reaction equation
[CH2:1]([C:7]1([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:12]2[S:13][CH2:14][CH2:15][C:11]=2[C:10]2[C:16]([OH:21])=[CH:17][C:18]([CH3:20])=[CH:19][C:9]=2[O:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[BrH:28].[N:29]1([CH2:34][CH2:35][CH2:36][C:37](O)=[O:38])[CH2:33][CH2:32][CH2:31][CH2:30]1.C1(N=C=NC2CCCCC2)CCCCC1>>[BrH:28].[CH2:22]([C:7]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:12]2[S:13][CH2:14][CH2:15][C:11]=2[C:10]2[C:16]([O:21][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:17][C:18]([CH3:20])=[CH:19][C:9]=2[O:8]1)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 214338814,4-di(1-hexyl)-1,2-dihydro-9-hydroxy-7-methyl-4H-thieno[2,3-c][1]benzopyranHCID 68132093gamma-Pyrrolidinobutyric acid hydrobromide salt

Product 1

HCID 681446024,4-di(1-Hexyl)-1,2-dihydro-7-methyl-9-[4-(pyrrolidino) butyryloxy]-4H-thieno[2,3-c][1]benzopyran hydrobromide

Procedure

By reacting 1,2-dihydro-9-hydroxy-7-methyl-4-oxo-4H-thieno[2,3-c][1]benzopyran with n-hexyl magnesium bromide, using the procedure described in Example 8, there is obtained 4,4-di(1-hexyl)-1,2-dihydro-9-hydroxy-7-methyl-4H-thieno [2,3-c][1]benzopyran. The benzopyran is then reacted with γ-pyrrolidinobutyric acid, hydrobromide salt and dicyclohexylcarbodiimide according to the method of Example 10 to yield the desired ester.

Sources & evidence

ORD record
ord-6423ec312c5a4f0c9dc427bf815a28b2
Source dataset
uspto-grants-1976_06
Patent number
US03960871

Reaction notes

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