Methanethiol → 3-(1-Methylthiotridecyl)-5-trimethylsilylfuran

HRID 1534345Notes

Reaction equation

HRID 1534345 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].[CH3:24][SH:25].C[O-].[K+]>O1CCCC1>[CH3:24][S:25][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]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 150370763-(1-Chlorotridecyl)-5-trimethylsilylfuranHCID 23664618Potassium methoxide

Product 1

HCID 199095103-(1-Methylthiotridecyl)-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(1-chlorotridecyl)-5-trimethylsilylfuran, methyl mercaptan and potassium methoxide in tetrahydrofuran is stirred at room temperature to give 3-(1-methylthiotridecyl)-5-trimethylsilylfuran. Oxidizing using Rose Bengal by the procedure of Example 1 gives 4-(1-methylthiotridecyl)-5-hydroxy-2(5H)-furanone.

Sources & evidence

ORD record
ord-50fa24e29c8b492daa3eb40af4dfcf44
Source dataset
uspto-grants-1992_02
Patent number
US05089485

Reaction notes

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