Methyl chloroformate → (E)-1-(2-Trimethylsilyl-4-furyl)-2-carbomethoxy-tridec-1-ene

HRID 1032274Notes

Reaction equation

HRID 1032274 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Br-].[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].Cl[C:44]([O:46][CH3:47])=[O:45].[CH3:48][Si:49]([CH3:58])([CH3:57])[C:50]1[O:54][CH:53]=[C:52]([CH:55]=O)[CH:51]=1>C1(C)C=CC=CC=1.O1CCCC1>[CH3:48][Si:49]([CH3:58])([CH3:57])[C:50]1[O:54][CH:53]=[C:52](/[CH:55]=[C:12](/[C:44]([O:46][CH3:47])=[O:45])\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:51]=1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 84955Dodecyltriphenylphosphonium bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Product 1

HCID 19991610(E)-1-(2-Trimethylsilyl-4-furyl)-2-carbomethoxy-tridec-1-ene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium bis(trimethylsilyl)amide (a 0.5 M solution in toluene; 14.5 ml, 7.24 mmol) was added to a solution of dodecyltriphenylphosphonium bromide (1.82 g, 3.56 mmol) in tetrahydrofuran (10 ml) at -78° under argon. After one hour, methyl chloroformate (0.28 ml, 3.56 mmol) was added, followed by 5-trimethylsilyl-3-furaldehyde (300 mg, 1.78 mmol) after one hour. Stirring was continued overnight while the cooling bath attained room temperature. The mixture was quenched with methanol/water (30 ml, 1:1). Extraction (ethyl ether/hexane, 1:1) and evaporation of the dried (magnesium sulfate) extracts gave an oil, which was flash chromatographed on silica using 20% ethyl ether/hexane. The title ester was obtained as a pale yellow oil.

Workup

  1. waitwas continued overnight while the cooling bath attained room temperature
  2. customThe mixture was quenched with methanol/water (30 ml, 1:1)
  3. extractionExtraction (ethyl ether/hexane, 1:1) and evaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil, which
  6. customchromatographed on silica using 20% ethyl ether/hexane

Sources & evidence

ORD record
ord-9f7f664172c246c1857a6f17de644760
Source dataset
uspto-grants-1990_09
Patent number
US04957917

Reaction notes

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