5-(Trimethylsilyl)furan-3-carbaldehyde → 3-(1-Hydroxytridecyl)-5-trimethylsilylfuran

HRID 727949Notes

Reaction equation

HRID 727949 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[O:7][CH:6]=[C:5]([CH:8]=[O:9])[CH:4]=1.[CH2:12]([Mg]Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>O1CCCC1>[OH:9][CH:8]([C:5]1[CH:4]=[C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])[O:7][CH:6]=1)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

4

Reactant 2

HCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178443215HCID 178443215, compound

Product 1

HCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-trimethylsilyl-3-furaldehyde (0.5 g, 2.97 mmol) in tetrahydrofuran (5 ml) was added to a solution of dodecyl magnesium bromide (5.95 mmol; prepared from 1.48 g dodecyl bromide and 146 mg magnesium turnings in 30 ml tetrahydrofuran) at room temperature. After 2 hours, the mixture was quenched with ammonium chloride solution and extracted thoroughly with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was flash chromatographed on silica using 10% ethyl ether/hexane. Fractions with Rf about 0.13 on evaporation gave the title alcohol as a pale yellow oil.

Workup

  1. customthe mixture was quenched with ammonium chloride solution
  2. extractionextracted thoroughly with ethyl ether
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil which
  6. customchromatographed on silica using 10% ethyl ether/hexane
  7. customFractions with Rf about 0.13 on evaporation

Sources & evidence

ORD record
ord-cf2efc4d6f604938a9b3404167957f49
Source dataset
uspto-grants-1991_09
Patent number
US05045564

Reaction notes

Loading…