Tetrabutylammonium Fluoride → HCID 70298568, compound

HRID 1106910Notes

Reaction equation

HRID 1106910 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:39]3[CH:40]=[CH:41][O:42][C:38]=3[CH:37]=[CH:36][CH:35]=2)[CH3:31])[CH2:16][CH: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].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[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:39]3[CH:40]=[CH:41][O:42][C:38]=3[CH:37]=[CH:36][CH:35]=2)[CH3:31])[CH2:16][CH:17]2[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70295782HCID 70295782, compound

Product 1

HCID 70298568HCID 70298568, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 36 (0.90 g, 1.45 mmol) in tetrahydrofuran (10 mL) was added tetrabutylammonium fluoride (1.0 M in tetrahydrofuran) (1.45 mL, 1.45 mmol). The reaction was stirred at room temperature under argon for 2.5 hours, then half the solvent was removed in vacuo. After stirring for a further 30 minutes, the reaction was poured into water (15 mL) and brine (70 mL), and extracted with dichloromethane (3×70 mL). The organics were dried (MgSO4) and the solvent removed in vacuo. Column chromatography (ethyl acetate:methanol 4:1) gave the product as a clear oil, 1.32 mmol, 90%.

Workup

  1. customhalf the solvent was removed in vacuo
  2. stirringAfter stirring for a further 30 minutes
  3. additionthe reaction was poured into water (15 mL) and brine (70 mL)
  4. extractionextracted with dichloromethane (3×70 mL)
  5. dry with materialThe organics were dried (MgSO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-96a25ff417b3432cb1c924dd54af39e6
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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