Tetrabutylammonium Fluoride → HCID 18930715, compound

HRID 1598817Notes

Reaction equation

HRID 1598817 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:35]=[CH:36][CH:37]=1)[C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([O:27][Si](C(C)(C)C)(C)C)[CH:21]=[CH:20]2)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:35]=[CH:36][CH:37]=1)[C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20]2)=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18930713HCID 18930713, compound

Product 1

HCID 18930715HCID 18930715, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Silyl ether 330d (1.0 g, 1.9 mmol) and tetrabutylammonium fluoride (1M in THF, 1.9 mL, 1.9 mmol) were stirred in THF (40 mL) at room temperature under N2 for 2h. After solvent evaporation, the mixture was extracted with EtOAc and 5% aq. KHSO4, then water, finally brine. Concentration and chromatography on silica gel, eluting with 0% to 40% EtOAc in hexane yielded, after drying, a colorless foam (0.70 g). IR(KBr): cm-1 3334, 1686. MS(NH3): 425 (M+NH4), 402 (M+H).

Workup

  1. customAfter solvent evaporation
  2. extractionthe mixture was extracted with EtOAc and 5% aq. KHSO4
  3. concentrationConcentration and chromatography on silica gel
  4. washeluting with 0% to 40% EtOAc in hexane
  5. customyielded
  6. customafter drying

Sources & evidence

ORD record
ord-8e3b9f4502de432e82c2b31df8dbd3ea
Source dataset
uspto-grants-1998_04
Patent number
US05739163

Reaction notes

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