Methyl iodide → 4-(1-Methoxytridecyl)-2-trimethylsilylfuran

HRID 1090887Notes

Reaction equation

HRID 1090887 reaction equation
[OH:1][CH:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:18][CH:19]=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].[H-].[Na+].I[CH3:27]>O1CCCC1.C(OCC)C>[CH3:27][O:1][CH:2]([C:15]1[CH:16]=[C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:18][CH:19]=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

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuran

Product 1

HCID 150370584-(1-Methoxytridecyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (318.5 mg, 0.9 mmol), sodium hydride (60% dispersion in oil; 150 mg, 3.8 mmol) and iodomethane (0.29 ml, 4.7 mmol) in tetrahydrofuran (7 ml) was refluxed for 16 hours. On cooling, the mixture was diluted with ethyl ether (20 ml), quenched with methanol (2 ml) and washed with water. Evaporation of the dried (magnesium sulfate) organic phase gave a deep yellow oil, identified as 4-(1-methoxytridecyl)-2-trimethylsilyfuran.

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperatureOn cooling
  3. customquenched with methanol (2 ml)
  4. washwashed with water
  5. customEvaporation of the
  6. dry with materialdried (magnesium sulfate) organic phase
  7. customgave a deep yellow oil

Sources & evidence

ORD record
ord-d498d68589154181849a5daaeed9b4d9
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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