P,P-Diphenylphosphinic azide → 3-(1-Azidotridecyl)-2-triethylsilylfuran

HRID 1090930Notes

Reaction equation

HRID 1090930 reaction equation
O[CH:2]([C:15]1[CH:19]=[CH:18][O:17][C:16]=1[Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C1(P([N:41]=[N+:42]=[N-:43])(C2C=CC=CC=2)=O)C=CC=CC=1>>[N:41]([CH:2]([C:15]1[CH:19]=[CH:18][O:17][C:16]=1[Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N+:42]=[N-:43]

Participants

3

Reactant 2

HCID 199401P,P-Diphenylphosphinic azideHCID 190199073-(1-Hydroxytridecyl)-2-triethylsilylfuran

Product 1

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

Procedure

Reacting 3-(1-hydroxytridecyl)-2-triethylsilylfuran with diphenylphosphoryl azide and diethyl azidocarboxylate gives 3-(1-azidotridecyl)-2-triethylsilylfuran. Reducing this intermediate with lithium aluminum hydride, followed by acetylation with acetic anhydide gives 3-(1-acetamido tridecyl)-2-triethylsilylfuran. Singlet oxygen oxidation of this amide, followed by reduction with sodium borohydride gives 3-(1-acetamidotridecyl)-2(5H)-furanone.

Sources & evidence

ORD record
ord-8570cf08d4ef4a98a7509c0d98f43177
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

Loading…