Acetic Anhydride → 5-Methyl-4-(1-acetoxytridecyl)-2-trimethylsilylfuran

HRID 1109895Notes

Reaction equation

HRID 1109895 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][C:16]1[O:20][C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:18][C:17]=1[CH:25]=[O:26].[C:27](OC(=O)C)(=[O:29])[CH3:28]>O1CCCC1>[CH3:15][C:16]1[O:20][C:19]([Si:21]([CH3:22])([CH3:24])[CH3:23])=[CH:18][C:17]=1[CH:25]([O:26][C:27](=[O:29])[CH3:28])[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 7918Acetic AnhydrideHCID 89191-BromododecaneHCID 5462224MagnesiumHCID 157445905Methyl-2-trimethylsilyl-4-furaldehyde

Product 1

HCID 194331855-Methyl-4-(1-acetoxytridecyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-bromododecane (261 mg, 0.11 mmol) and magnesium turnings (27 mg, 0.11 mmol) in tetrahydrofuran (7 ml) was refluxed under argon for 1 hour. After cooling to room temperature, a solution of 5-methyl-2-trimethylsilyl-4-furaldehyde (158.6 mg, 0.87 mmol) in tetrahydrofuran (1 ml) was added, followed by acetic anhydride (0.25 ml, 2.6 mmol) after 1 hour. Stirring was continued at room temperature overnight and the mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative TLC (20×20 cm, 1000 micron silica plate; developed with 5% ethyl ether/hexane). The title ester was obtained as a light yellow oil.

Workup

  1. temperaturewas refluxed under argon for 1 hour
  2. customthe mixture was quenched with water
  3. extractionExtraction (ethyl ether) and evaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customwas purified by preparative TLC (20×20 cm, 1000 micron silica plate; developed with 5% ethyl ether/hexane)

Sources & evidence

ORD record
ord-85e27b27a0844e5b9d4acaa68ad51c84
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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