Phenol → 3-(1-Phenoxytridecyl)-5-trimethylsilylfuran

HRID 1534344Notes

Reaction equation

HRID 1534344 reaction equation
Cl[CH:2]([C:15]1[CH:19]=[C:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:17][CH:16]=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].[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C[O-].[K+]>O1CCCC1>[O:30]([CH:2]([C:15]1[CH:19]=[C:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:17][CH:16]=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])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 150370763-(1-Chlorotridecyl)-5-trimethylsilylfuranHCID 23664618Potassium methoxide

Product 1

HCID 199095083-(1-Phenoxytridecyl)-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(1-chlorotridecyl)-5-trimethylsilylfuran, phenol and potassium methoxide in tetrahydrofuran is stirred at room temperature to give 3-(1-phenoxytridecyl)-5-trimethylsilylfuran. A mixture of this intermediate and Rose Bengal in tetrahydrofuran is exposed to oxygen by the procedure of Example 1 to give 4-(1-phenoxytridecyl)-5-hydroxy-2(5H)-furanone.

Sources & evidence

ORD record
ord-20a2e5caba7744579d087991b4cbb4a5
Source dataset
uspto-grants-1992_02
Patent number
US05089485

Reaction notes

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