Water → HCID 59389336, compound

HRID 2357943Notes

Reaction equation

HRID 2357943 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Si]([O:31][CH2:32][C:33]1[C:34]2[N:35]([N:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=2)[C:36]([CH2:39][O:40][CH3:41])=[CH:37][CH:38]=1)(C(C)(C)C)(C)C.O>O1CCCC1>[OH:31][CH2:32][C:33]1[C:34]2[N:35]([N:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=2)[C:36]([CH2:39][O:40][CH3:41])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 58014019HCID 58014019, compound

Product 1

HCID 59389336HCID 59389336, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 1 mol/L tetrabutylammonium fluoride-tetrahydrofuran solution (35.1 mL) was added dropwise to a solution of the compound of Example 325 (8.76 g) in tetrahydrofuran (120 mL) at 0° C. The mixture was stirred at 0° C. for 30 min. Subsequently, water was added and the mixture was extracted with ethyl acetate (300 mL). The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. The extract was concentrated and purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to afford the title compound as a colorless powder (6.00 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (300 mL)
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe extract was concentrated
  5. custompurified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b31e7e7e7c5642df8701eddff4ac7773
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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