Fluoride Ion → HCID 69710363, compound

HRID 2121914Notes

Reaction equation

HRID 2121914 reaction equation
[C:1]([O:5][C:6]([CH:8]1[O:30][C:11]2=[CH:12][CH:13]=[C:14]3[C:18]([N:17]([CH2:19][C@H:20]([O:22][Si](C(C)(C)C)(C)C)[CH3:21])[N:16]=[CH:15]3)=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C(=O)(O)[O-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([CH:8]1[O:30][C:11]2=[CH:12][CH:13]=[C:14]3[C:18]([N:17]([CH2:19][C@H:20]([OH:22])[CH3:21])[N:16]=[CH:15]3)=[C:10]2[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 28179Fluoride IonHCID 516892Sodium BicarbonateHCID 69710152HCID 69710152, compound

Product 1

HCID 69710363HCID 69710363, compoundYield 115.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of the product from Step C (0.46 g, 1.06 mmol) in THF (50 mL) was added tetrabutylammnium fluoride (1 N in THF, 2.13 mL, 2.13 mmol). The mixture was combined with a saturated aqueous solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate. Chromatography on silica (gradient, 20% to 70% ethyl acetate in hexane) gave an oil (0.39 g): LC/MS (+ESI) m/z 319 (M+H).

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-c97dd758cee04563a54ae3b54831c42d
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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