Bromine → (E)-4-(2-Bromo-1-tridecenyl)-2-trimethylsilylfuran

HRID 1032275Notes

Reaction equation

HRID 1032275 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Br-:11].[CH2:12]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].BrBr.[CH3:45][Si:46]([CH3:55])([CH3:54])[C:47]1[O:51][CH:50]=[C:49]([CH:52]=O)[CH:48]=1>C1(C)C=CC=CC=1.O1CCCC1.CO.O>[Br:11]/[C:12](/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:52]/[C:49]1[CH:48]=[C:47]([Si:46]([CH3:55])([CH3:54])[CH3:45])[O:51][CH:50]=1

Participants

8

Reactant 4

HCID 24408BromineHCID 84955Dodecyltriphenylphosphonium bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Product 1

HCID 22165558(E)-4-(2-Bromo-1-tridecenyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×HCID 22242641Methanol--water (1/1)Solvent

Procedure

Potassium bis(trimethylsilyl)amide (a 0.5M solution in toluene; 6 ml, 3.02 mmol) was added dropwise to a solution of dodecyltriphenylphosphonium bromide (761 mg, 1.49 mmol) in tetrahydrofuran (10 ml) at -78° under argon. After 2 hours, a solution of bromine (81 μl , 1.49 mmol) in tetrahydrofuran (1 ml) was added. followed by a solution of 5-trimethylsilyl-3-furaldehyde (250 mg, 1.49 mmol) in tetrahydrofuran (1 ml) after 1 hour. Stirring was continued at room temperature for 2 days and the mixture was poured into methanol/water (30 ml, 1:1). Extraction (ethyl ether/hexane, 1:1) and evaporation of the dried extracts (magnesium sulphate) gave an oil which was chromatographed on silica using 10% ethyl ether/hexane. Fractions with Rf of about 0.71 on evaporation afforded the title alkene as a pale yellow oil.

Workup

  1. waitwas continued at room temperature for 2 days
  2. extractionExtraction (ethyl ether/hexane, 1:1) and evaporation of the dried extracts (magnesium sulphate)
  3. customgave an oil which
  4. customwas chromatographed on silica using 10% ethyl ether/hexane
  5. customFractions with Rf of about 0.71 on evaporation

Sources & evidence

ORD record
ord-5888a91a17ce40aebe61c000623e1a98
Source dataset
uspto-grants-1990_09
Patent number
US04957917

Reaction notes

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