Oxygen → HCID 19019891, compound

HRID 2249298Notes

Reaction equation

HRID 2249298 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:9].[C:31]([NH:34][CH:35]([C:48]1[CH:52]=[CH:51][O:50][C:49]=1[Si](CC)(CC)CC)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])(=[O:33])[CH3:32].O=O.[BH4-].[Na+]>>[C:31]([NH:34][CH:35]([C:48]1[C:49](=[O:9])[O:50][CH2:51][CH:52]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])(=[O:33])[CH3:32]

Participants

6

Reactant 5

HCID 977OxygenHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 4311764Sodium borohydrideHCID 19019862HCID 19019862, compound2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 19019891HCID 19019891, compound

Procedure

Reacting 3-(1-hydroxytridecyl)-2-triethylsilylfuran (Compound 20) with diphenylphosphoryl azide and diethyl azidocarboxylate gives 3-(1-azidotridecyl)-2-triethylsilylfuran (Compound 24). Reducing this intermediate with lithium aluminum hydride, followed by acetylation with acetic anhydide gives 3-(1-acetamido tridecyl)-2-triethylsilylfuran (Compound 25). Singlet oxygen oxidation of this amide, under conditions as in Example 1, followed by reduction with sodium borohydride gives 3-(1-acetamidotridecyl)-2(5H)-furanone (Compound 10).

Sources & evidence

ORD record
ord-6f5c70657962401ab07d407ea94b095c
Source dataset
uspto-grants-1991_08
Patent number
US05043457

Reaction notes

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