P,P-Diphenylphosphinic azide → 4-(1-Azidotridecyl)-2-triethylsilylfuran

HRID 727957Notes

Reaction equation

HRID 727957 reaction equation
O[CH:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[O:18][CH:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C1C=CC(P([N:41]=[N+:42]=[N-:43])(C2C=CC=CC=2)=O)=CC=1>>[N:41]([CH:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[O:18][CH:19]=1)[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 156632694-(1-Hydroxytridecyl)-2-triethylsilylfuran

Product 1

HCID 194331464-(1-Azidotridecyl)-2-triethylsilylfuran

Procedure

Reacting 4-(1-hydroxytridecyl)-2-triethylsilylfuran with diphenylphosphonyl azide and diethyl azidocarboxylate gives 4-(1-azidotridecyl)-2-triethylsilylfuran. Reducing this azide with lithium aluminum hydride gives 4-(1-aminotridecyl)-2-triethylsilylfuran. Acetylation of this intermediate with acetic anhydride gives 4-(1-acetamido)tridecyl-2-triethylsilylfuran. Oxidizing this amide with oxygen using Rose Bengal as an initiator gives 4-(1-acetamido)-5-hydroxy-2(5H)-furanone. Reduction of this furanone with sodium borohydride gives 4-(1-acetamido)-2(5H)-furanone.

Sources & evidence

ORD record
ord-98ca30cdcc7f4ebb8d3644ccaa1e57b1
Source dataset
uspto-grants-1991_09
Patent number
US05045564

Reaction notes

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