3-(1-Hydroxytridecyl)-5-trimethylsilylfuran → 4-[1-(Dodecanoyloxy)tridecyl]2-trimethylsilylfuran

HRID 654929Notes

Reaction equation

HRID 654929 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])C.[OH:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CCCCC.O1CCCC1>[C:7]([O:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:6])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:3][CH2:1][CH3:4]

Participants

5

Reactant 2

HCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuranHCID 178418306HCID 178418306, compound

Product 1

HCID 150370684-[1-(Dodecanoyloxy)tridecyl]2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl lithium (a 1.7M solution in pentane; 0.21 ml, 0.36 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (124.5 mg, 0.37 mmol) in tetrahydrofuran (5 ml) at 0° under argon. After 5 minutes, the cooling bath was removed and lauroyl chloride (88 μl) was added. The mixture was stirred at room temperature for 16 hours and 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, 1000μ silica plate; developed with 5% ethyl ether/hexane). The title ester was obtained as a colorless oil.

Workup

  1. customthe cooling bath was removed
  2. additionlauroyl chloride (88 μl) was added
  3. customquenched with water
  4. extractionExtraction (ethyl ether) and evaporation of the
  5. dry with materialdried (magnesium sulphate)
  6. customextracts gave an oil, which
  7. customwas purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 5% ethyl ether/hexane)

Sources & evidence

ORD record
ord-c48ebb1a9eb344f8bebd5fe9ea9cc3c5
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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