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

HRID 488211Notes

Reaction equation

HRID 488211 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 1.7 M 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 degrees under argon. After 10 minutes, cyclohexanecarboxylic acid chloride (74 microliter, 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, 1000u 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, 1000u silica plate; developed with 5% ethyl ether/hexane)

Sources & evidence

ORD record
ord-260cecdc03a7458cade32750e31a1272
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Reaction notes

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