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

HRID 1090891Notes

Reaction equation

HRID 1090891 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 degrees under argon. After 5 minutes, the cooling bath was removed and lauroyl chloride (88 microliter) 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, 1000u 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 microliter) 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, 1000u silica plate; developed with 5% ethyl ether/hexane)

Sources & evidence

ORD record
ord-f3268e36a7a44ed5b5b950270bf97877
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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