Methanesulfonyl chloride → HCID 19019875, compound

HRID 1090932Notes

Reaction equation

[N:1]([CH:4]([C:17]1[CH:21]=[CH:20][O:19][C:18]=1[Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:35][S:36](Cl)(=[O:38])=[O:37]>>[CH3:35][S:36]([NH:1][CH:4]([C:17]1[CH:21]=[CH:20][O:19][C:18]=1[Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:38])=[O:37]

Participants

Reactant 3

HCID 31297Methanesulfonyl chloride

HCID 190198873-(1-Azidotridecyl)-2-triethylsilylfuran

HCID 21226445Aluminium lithium hydride

Product 1

HCID 19019875HCID 19019875, compound

Procedure

Reducing 3-(1-azidotridecyl)-2-triethylsilylfuran with lithium aluminum hydride, as in Example 8, followed by reacting the intermediate with methanesulfonyl chloride, gives 3-(1-methanesulfonamidotridecyl)-2-triethylsilylfuran. Oxidizing this sulfonamide followed by reduction with sodium borohydride gives 3-(1-methanesulfonamidotridecyl)-2(5H)-furanone.

Sources & evidence

ORD record: ord-27f1d845f6c54f1a8198db1c86a1e4c2
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05082954

Reaction notes

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