1-Bromododecane → HCID 15728729, compound

HRID 1492937Notes

Reaction equation

HRID 1492937 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Mg].[CH3:15][Si:16]([CH3:25])([CH3:24])[C:17]1[O:21][CH:20]=[C:19]([CH:22]=[O:23])[CH:18]=1.[CH3:26][O:27][CH2:28][CH2:29][O:30][CH2:31]Cl>O1CCCC1>[CH3:26][O:27][CH2:28][CH2:29][O:30][CH2:31][O:23][CH:22]([C:19]1[CH:18]=[C:17]([Si:16]([CH3:25])([CH3:24])[CH3:15])[O:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 89191-BromododecaneHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 5462224MagnesiumHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Product 1

HCID 15728729HCID 15728729, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-bromododecane (222 mg, 0.89 mmol) and magnesium turnings (22 mg, 0.94 mmol) in tetrahydrofuran (5 ml) was refluxed under argon for 1 hour. After cooling to 0°, a solution of 5-trimethylsilyl-3-furaldehyde (150 mg, 0.89 mmol) in tetrahydrofuran (1 ml) was added and conditions maintained for 1 hour. 2-Methoxyethoxymethyl chloride (0.15 ml, 1.34 mmol) was added and stirring was continued at room temperature for 16 hours. The mixture was quenched with water and extracted with ethyl ether. Evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative TLC (silica plate; developed with 15% ethyl ether/petroleum ether). The title trimethylsilylfuran was obtained as a pale yellow oil.

Workup

  1. temperaturewas refluxed under argon for 1 hour
  2. temperatureAfter cooling to 0°
  3. temperatureconditions maintained for 1 hour
  4. customThe mixture was quenched with water
  5. extractionextracted with ethyl ether
  6. customEvaporation of the
  7. dry with materialdried (magnesium sulphate)
  8. customextracts gave an oil, which
  9. customwas purified by preparative TLC (silica plate; developed with 15% ethyl ether/petroleum ether)

Sources & evidence

ORD record
ord-f28da0ac77c148adb3e85b7b0b2f1963
Source dataset
uspto-grants-1994_12
Patent number
US05376676

Reaction notes

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