HCID 19991617, compound → HCID 19991589, compound

HRID 345889Notes

Reaction equation

HRID 345889 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:16]=[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])[O:14][CH:13]=1.C[C:22](C)=[O:23].[OH:25]S(O)(=O)=O.O=[Cr](=O)=O>>[C:22]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:16]=[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])[O:14][CH:13]=1)([OH:23])=[O:25]

Participants

3

Reactant 2

HCID 19991617HCID 19991617, compoundHCID 131709961Jones' reagent

Product 1

HCID 19991589HCID 19991589, compound

Procedure

3-(10-Hydroxydecyl)-5-trimethylsilylfuran is oxidized by Jones reagent (chromic acid) to give 3-(10-carboxydecyl)-5-trimethylsilylfuran. A mixture of this compound and Rose Bengal in tetrahydrofuran is exposed to singlet oxygen at -78° to give 4-(10-carboxydecyl)-5-hydroxy-2(5H)-furanone.

Sources & evidence

ORD record
ord-bfc8085ab612427ca308d685be21d54d
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

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