Diethyl Ether → Tetrabutylammonium Fluoride

HRID 853611Notes

Reaction equation

HRID 853611 reaction equation
[F:1]C1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:19](=O)[C:18]3[C:17](O[Si](CC)(CC)CC)=[C:16]4[C:11](C=CC=N4)=[C:10](O)[C:9]=3[C:8]2=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CCO[CH2:42][CH3:43].[CH2:44]([CH2:47]OC)OC>>[F-:1].[CH2:44]([N+:7]([CH2:6][CH2:5][CH2:31][CH3:32])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:19][CH2:18][CH2:17][CH3:16])[CH2:47][CH2:42][CH3:43]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 136158592HCID 136158592, compound

Product 1

HCID 2724141Tetrabutylammonium Fluoride

Procedure

For example, 7-(4-fluoro-benzyl)-5-hydroxy-9-triethylsilanyloxy-pyrrolo[3,4-g]quinoline-6,8-dione A6.6, (Example 12, Scheme 11) is reacted at ambient temperature in dimethoxyethane solution with one molar equivalent of a dialkyl 4-bromo-2-butenylphosphonate A6.7 (J. Med. Chem., 1992, 35, 1371) and potassium carbonate, to yield the ether product A6.8, which upon deprotection with tetrabutylammonium fluoride gives the phenol A6.9.

Sources & evidence

ORD record
ord-b004664a3900406aa44a240662d44ce0
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

Loading…