1-Bromododecane → HCID 15728729, compound

HRID 1534337Notes

Reaction equation

HRID 1534337 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 mol) 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 contained at room temperature for 16 hours. The mixture was quenched with water and extracted with ethyl ether. Evaporating of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 15% ethyl ether/petroleum ether). The little 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. customEvaporating of the
  7. dry with materialdried (magnesium sulphate)
  8. customextracts gave an oil, which
  9. customwas purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 15% ethyl ether/petroleum ether)

Sources & evidence

ORD record
ord-db700da6e10e4f038fe8d0f012ba7b9a
Source dataset
uspto-grants-1992_02
Patent number
US05089485

Reaction notes

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