Tetrabutylammonium Fluoride → HCID 11249305, compound

HRID 1353190Notes

Reaction equation

HRID 1353190 reaction equation
[CH2:1]([O:3][C:4](=[O:46])[C@@H:5]([O:43][CH2:44][CH3:45])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[C:16](/[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:42])=[CH:31][CH2:32][O:33]C[Si](C(C)(C)C)(C)C)=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)\[CH3:17])=[CH:9][CH:8]=1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:46])[C@@H:5]([O:43][CH2:44][CH3:45])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14]/[CH:15]=[C:16](/[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27](/[C:30](/[CH3:42])=[CH:31]/[CH2:32][OH:33])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)\[CH3:17])=[CH:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86588416HCID 86588416, compound

Product 1

HCID 11249305HCID 11249305, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of E)(E)(S) 3-{4-[3-(4′-{3-[(tert-butyidimethylsilanyl)-methoxy]-1-methylpropenyl}-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester (1.18 g, 1.84 mmol) in dry THF was cooled on ice and slowly added a 1.1M solution of tetrabutylammonium fluoride in THF (1.93 mL, 1.93 mmol). The reaction mixture was stirred at room temperature for 3 h. The mixture was diluted with water and ethyl acetate, the aqueous layer collected and further extracted with ethyl acetate. The organic layers were combined, washed with brine, dried (MgSO4) and evaporated to give 0.94 g of (E)(E)(S) 2-ethoxy-3-(4-{3-[4′-{3-hydroxy-1-methyl-propenyl)-biphenyl-4-yl]-but-2-enyloxy}-phenyl)-propionic acid ethyl ester.

Workup

  1. customthe aqueous layer collected
  2. extractionfurther extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-27388c4b6aaa4f378c8d66e1b9fb5417
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

Loading…