Tetrahydrofuran → 4-Dodecanoxy-2-triethylsilylfuran

HRID 1109862Notes

Reaction equation

HRID 1109862 reaction equation
OC[C:3]1[CH:4]=[C:5]([Si:8]([CH2:13][CH3:14])([CH2:11][CH3:12])[CH2:9][CH3:10])[O:6][CH:7]=1.[H-].[K+].I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[O:30]1CCCC1>>[CH2:18]([O:30][C:3]1[CH:4]=[C:5]([Si:8]([CH2:9][CH3:10])([CH2:11][CH3:12])[CH2:13][CH3:14])[O:6][CH:7]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 202821-IodododecaneHCID 82127Potassium hydride2×HCID 150370354-Hydroxymethyl-2-triethylsilylfuran2×

Product 1

HCID 190198574-Dodecanoxy-2-triethylsilylfuran

Procedure

A solution of 4-hydroxymethyl-2-triethylsilylfuran (Compound 1, 160 mg, 0.75 mmol) in tetrahydrofuran (0.5 ml) was added to a suspension of potassium hydride (33 mg, 0.83 mmol) in tetrahydrofuran (1 ml) at room temperature. When all the potassium hydride disappeared, 1-iodododecane (0.37 ml, 1.5 mmol) was added. Stirring was continued for 4 days at room temperature. The reaction mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 5% ethyl ether/hexane. Fractions with Rf of about 0.65 on evaporation gave the titled ether as a pale yellow oil.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionExtraction (ethyl ether) and evaporation of the
  3. dry with materialdried (magnesium sulfate)
  4. customextracts gave an oil, which
  5. customwas purified by flash chromatography on silica using 5% ethyl ether/hexane
  6. customFractions with Rf of about 0.65 on evaporation
  7. customgave the titled ether as a pale yellow oil

Sources & evidence

ORD record
ord-9361abcd3ed443dc8b4df34d2a3235d0
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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