Tetrabutylammonium Fluoride → HCID 24820475, compound

HRID 1191943Notes

Reaction equation

HRID 1191943 reaction equation
[Si]([O:8][CH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[S:19][CH:20]=[CH:21][N:22]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[S:19]1[CH:20]=[CH:21][N:22]=[C:18]1[C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[CH:9]([OH:8])[CH2:10][CH2:11]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 248204742-[1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2,3-dihydro-1H-inden-5-yl]thiazole

Product 1

HCID 24820475HCID 24820475, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(1-{[tert-butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-5-yl)-1,3-thiazole (630 mg, 1.9 mmol) in tetrahydrofuran (10.00 mL) was added a 1.00 M solution of tetrabutylammonium fluoride, trihydrate in tetrahydrofuran (1.90 mL) at 0° C. The ice bath was removed and the reaction mixture was stirred at room temperature for 1 h. The mixture was diluted with ether, washed with saturated NaCl aqueous solution, dried over anhydrous MgSO4, filtered and evaporated under reduced pressure to afford the desired product (410 mg, 99%).

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was diluted with ether
  3. washwashed with saturated NaCl aqueous solution
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ad673eda6e5747e3a62ab78de3fcdc2a
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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