Cyclohexanecarbonyl chloride → 4-[1-(Cyclohexanoyloxy)tridecyl]-2-trimethylsilylfuran

HRID 654928Notes

Reaction equation

HRID 654928 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].[CH:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CCCCC.O1CCCC1>[CH:29]1([C:35]([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:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 75938Cyclohexanecarbonyl chlorideHCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuranHCID 178418306HCID 178418306, compound

Product 1

HCID 150370664-[1-(Cyclohexanoyloxy)tridecyl]-2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl lithium (a 1.7M solution in pentane; 0.33 ml, 0.55 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (170 mg, 0.50 mmol) in tetrahydrofuran (5 ml) at 0° under argon. After 10 minutes, cyclohexanecarboxylic acid chloride (74 μl, 0.55 mmol) was added. The mixture was stirred at room temperature for 15 hours and quenched with water. Extraction 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 pale yellow oil.

Workup

  1. customquenched with water
  2. extractionExtraction and evaporation of the
  3. dry with materialdried (magnesium sulphate)
  4. customextracts gave an oil, which
  5. customwas purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 5% ethyl ether/hexane)

Sources & evidence

ORD record
ord-6295177ffe2546988c94a272aef94b35
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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