Water → HCID 72410012, compound

HRID 723464Notes

Reaction equation

HRID 723464 reaction equation
[Si]([O:8][CH:9]1[CH:15]2[CH:13]([O:14]2)[CH2:12][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[OH:8][CH:9]1[CH:15]2[CH:13]([O:14]2)[CH2:12][N:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 72410003HCID 72410003, compound

Product 1

HCID 72410012HCID 72410012, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Compound 239F (13.6 g, 45.1 mmol) in 10 mL of dry THF was added a solution of TBAF (67.6 mL, 67.6 mmol) in THF. The mixture was stirred overnight at room temperature. Water was added and the reaction mixture was extracted with EtOAc (250 mL×3). The combined organic layers were washed with brine and dried over anhydrous Na2SO4. Concentration in vacuo followed by flash chromatography (hexane-EtOAc: 1:1 to 1:2) on silica gel afforded 6.03 g (Yield: 75%) of 239H as an oil. 1H-NMR (400 MHz, CDCl3): 4.15 (m, 1H), 4.13 (q, J=7.08, 2H), 3.95 (m, 1H), 3.75 (m, 1H), 3.52 (m, 1H), 3.32 (m, 1H), 3.25 (m, 2H), 3.10 and 2.55 (partial, 1H), 1.27 (t, J=7.08, 3H).

Workup

  1. extractionthe reaction mixture was extracted with EtOAc (250 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-6ae108ca99ba425282bc8a15b78ade56
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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