3-(1-Hydroxytridecyl)-5-trimethylsilylfuran → HCID 19909501, compound

HRID 1534343Notes

Reaction equation

HRID 1534343 reaction equation
C([Li])(C)(C)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].[I:29][CH2:30][CH2:31][CH2:32][C:33](Cl)=[O:34]>CCCCC.O1CCCC1>[I:29][CH2:30][CH2:31][CH2:32][C:33]([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:34]

Participants

6

Reactant 3

HCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuranHCID 199094994-Iodobutanoyl chlorideHCID 178418306HCID 178418306, compound

Product 1

HCID 19909501HCID 19909501, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl lithium (a 1.7 M solution in pentane; 0.33 ml, 0.56 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (188.1 mg, 0.56 mmol) in tetrahydrofuran (4 ml) at 0° under argon. After 15 minutes, a solution of 4-iodobutyryl chloride (129 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued overnight while the cooling bath attained room temperature. The mixture was quenched with water and extracted with ethyl ether. Evaporation of the dried (magnesium sulphate) extracts afforded an oil, which was purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane). The title ester was obtained as a colorless oil.

Workup

  1. waitwas continued overnight while the cooling bath attained room temperature
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl ether
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulphate)
  6. customextracts afforded an oil, which
  7. customwas purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane)

Sources & evidence

ORD record
ord-5e898d088c3a44d48caaea003925f4d6
Source dataset
uspto-grants-1992_02
Patent number
US05089485

Reaction notes

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