4-Phenylbutanoyl Chloride → 4-[1-(4-Phenylbutanoyloxy)tridecyl]2-trimethylsilylfuran

HRID 654926Notes

Reaction equation

HRID 654926 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].[C:29]1([CH2:35][CH2:36][CH2:37][C:38](Cl)=[O:39])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CCCCC.O1CCCC1>[C:29]1([CH2:35][CH2:36][CH2:37][C:38]([O:6][CH:7]([C:20]2[CH:21]=[C:22]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:23][CH:24]=2)[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:39])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 117898654-Phenylbutanoyl ChlorideHCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuranHCID 178418306HCID 178418306, compound

Product 1

HCID 150370604-[1-(4-Phenylbutanoyloxy)tridecyl]2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl lithium (a 1.7M solution in pentane; 0.47 ml, 0.79 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (256.4 mg, 0.76 mmol), prepared as in Example 38, in tetrahydrofuran (5 ml) at -78° under argon. After 10 minutes, a solution of 4-phenylbutyryl chloride (145 mg, 0.79 mmol) was added. Stirring was continued at room temperature for 2 days and the mixture was quenched with water. Extraction and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative thin-layer chromatography (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane). The title ester was obtained as a light yellow oil.

Workup

  1. waitwas continued at room temperature for 2 days
  2. customthe mixture was quenched with water
  3. extractionExtraction and evaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customwas purified by preparative thin-layer chromatography (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane)

Sources & evidence

ORD record
ord-cad42599fb584e0a9e1cd02b767a418a
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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