Tetrabutylammonium Fluoride → HCID 87845477, compound

HRID 654546Notes

Reaction equation

HRID 654546 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([O:14][C:15](=[O:23])[NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][C:10]([CH3:25])([CH3:24])[C:9]=2/[CH:26]=[CH:27]/[C@@H:28]2[O:33][C:32](=[O:34])[CH2:31][C@@H:30]([O:35][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:29]2)=[CH:4][C:3]=1[CH3:53].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([O:14][C:15](=[O:23])[NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][C:10]([CH3:25])([CH3:24])[C:9]=2/[CH:26]=[CH:27]/[C@@H:28]2[O:33][C:32](=[O:34])[CH2:31][C@@H:30]([OH:35])[CH2:29]2)=[CH:4][C:3]=1[CH3:53]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131716812HCID 131716812, compound

Product 1

HCID 87845477HCID 87845477, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to Scheme V, 38 (0.20 gm) was treated with tetrabutylammonium fluoride in THF and acetic acid and, after workup, purified by SiO2 using 1:1 hexanes:EtOAc as eluent and yielded 0.101 g of product. mp 73°-5° C. Anal. C29H32FNO5 : Theory C: 70.57; H: 6.54; N:2.84. Found C: 70.37; H: 6.94; N: 3.06.

Workup

  1. customafter workup, purified by SiO2 using 1:1 hexanes

Sources & evidence

ORD record
ord-b2fe594b278842d1b5fd77205bb12f03
Source dataset
uspto-grants-1992_07
Patent number
US05132312

Reaction notes

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