Oxygen → HCID 19019891, compound

HRID 1681541Notes

Reaction equation

[O:1]=O.[C:3]([NH:6][CH:7]([C:20]1[CH:24]=[CH:23][O:22][C:21]=1[Si](CC)(CC)CC)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:5])[CH3:4].[BH4-].[Na+]>>[C:3]([NH:6][CH:7]([C:20]1[C:21](=[O:1])[O:22][CH2:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:5])[CH3:4]

Participants

Reactant 3

HCID 977Oxygen

HCID 4311764Sodium borohydride

HCID 19019862HCID 19019862, compound

Product 1

HCID 19019891HCID 19019891, compound

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-46d531088ecc4f1893dac8e7217ad2af
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05171863

Reaction notes

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