Tetrabutylammonium Fluoride → HCID 70299251, compound

HRID 1106907Notes

Reaction equation

HRID 1106907 reaction equation
[C:1]([O:5][C:6](=[O:44])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([N:30]([C:32](=[O:43])[CH2:33][C:34]2[O:35][C:36]3[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=3[CH:38]=2)[CH3:31])[CH2:16][N:17]2[CH2:21][CH2:20][CH:19]([O:22][Si](C(C)(C)C)(C)C)[CH2:18]2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:44])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([N:30]([C:32](=[O:43])[CH2:33][C:34]2[O:35][C:36]3[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=3[CH:38]=2)[CH3:31])[CH2:16][N:17]2[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70298402HCID 70298402, compound

Product 1

HCID 70299251HCID 70299251, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of Example 31 (1.659 g, 2.66 mmol) in THF (25 mL) at room temperature was added TBAF (2.8 mL of a 1 M solution in THF, 2.8 mmol). The reaction was stirred for 2.5 hours, then diluted with saturated brine (100 mL) and extracted with dichloromethane (4×120 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. Purification by column chromatography in ethyl acetate:methanol (9:1) gave the product as an oil. 0.824 g, 61%.

Workup

  1. extractionextracted with dichloromethane (4×120 mL)
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography in ethyl acetate:methanol (9:1)

Sources & evidence

ORD record
ord-94d0930ba65b469eb161471627997b4d
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

Loading…