Tetrabutylammonium Fluoride → HCID 70298693, compound

HRID 1106905Notes

Reaction equation

HRID 1106905 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[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[O:36][CH:35]=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.O.[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[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[O:36][CH:35]=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

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70298449HCID 70298449, compound

Product 1

HCID 70298693HCID 70298693, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of Example 26 (1.20 g, 1.93 mmol) in THF (15 mL) at room temperature was added TBAF (2 mL of a 1 M solution in THF, 2 mmol). The reaction was stirred for 2 hours, then diluted with water (20 mL) and saturated brine (80 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. Yield=0.797 g, 81%.

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-5ff1453578f34cdab74dc9b266acbce1
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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