Phenylacetyl chloride → 4-[1-(Phenylacetoxy)tridecyl]-2-trimethylsilylfuran

HRID 1090889Notes

Reaction equation

HRID 1090889 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][C:36](Cl)=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CCCCC.O1CCCC1>[C:29]1([CH2:35][C:36]([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:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuranHCID 178418306HCID 178418306, compound

Product 1

HCID 150370644-[1-(Phenylacetoxy)tridecyl]-2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl lithium (a 1.7M solution in pentane; 0.29 ml, 0.49 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (138.2 mg, 0.41 mmol) in tetrahydrofuran (7 ml) at -78 degrees under argon. After 25 minutes, a solution of phenylacetyl chloride (65 microliter, 0.49 mmol) in tetrahydrofuran (1/2 ml) was added. Stirring was continued 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, 500 micron silica plate; developed with 10% ethyl ether/hexane). The title ester was obtained as a pale yellow oil.

Workup

  1. waitwas continued at room temperature for 16 hours
  2. customquenched with water
  3. extractionExtraction (ethyl ether) and evaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customwas purified by preparative TLC (20×20 cm, 500 micron silica plate; developed with 10% ethyl ether/hexane)

Sources & evidence

ORD record
ord-318dd78b536f482687c2e07ee83fcfd2
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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