Dodecanoyl chloride → HCID 15728721, compound

HRID 727953Notes

Reaction equation

HRID 727953 reaction equation
C([Li])CCC.C([Sn]([CH2:19][O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])(CCCC)CCCC)CCC.[CH3:27][Si:28]([CH3:37])([CH3:36])[C:29]1[O:33][CH:32]=[C:31]([CH:34]=[O:35])[CH:30]=1.[C:38](Cl)(=[O:50])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]>CCCCCC.O1CCCC1>[C:38]([O:35][CH:34]([C:31]1[CH:30]=[C:29]([Si:28]([CH3:37])([CH3:36])[CH3:27])[O:33][CH:32]=1)[CH2:19][O:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26])(=[O:50])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

7

Reactant 4

HCID 8166Dodecanoyl chlorideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 15728720HCID 15728720, compoundHCID 178418339Butyllithium

Product 1

HCID 15728721HCID 15728721, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

n-Butyl lithium (a 1.6M solution in hexane; 0.74 ml, 1.18 mmol) was added to a solution of 2-methoxyethoxy-methyl tributylstannylmethyl ether (481.6 mg, 1.18 mmol) in tetrahydrofuran (5 ml) at -78° under argon. After 10 minutes, a solution of 5-trimethylsilyl-3-furaldehyde (198 mg, 1.18 mmol) was added, followed by lauroyl chloride (0.26 ml, 1.18 mmol) after 20 minutes. Stirring was continued at room temperature for 48 hours and the mixture was quenched with water. Extraction (ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed on silica using 20% ethyl ether/petroleum ether. Fractions with Rf of about 0.27 (30% ethyl ether/petroleum ether) on evaporation afforded the title ester as a pale yellow oil.

Workup

  1. waitwas continued at room temperature for 48 hours
  2. customthe mixture was quenched with water
  3. extractionExtraction (ether) and evaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customchromatographed on silica using 20% ethyl ether/petroleum ether
  7. customFractions with Rf of about 0.27 (30% ethyl ether/petroleum ether) on evaporation

Sources & evidence

ORD record
ord-637386894fa24973a3190f996b91507c
Source dataset
uspto-grants-1991_09
Patent number
US05045564

Reaction notes

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