Tetrabutylammonium Fluoride → HCID 58303876, compound

HRID 1404106Notes

Reaction equation

HRID 1404106 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].F[C:20]1[C:21]([O:33][CH3:34])=[C:22]2[C:26](=[CH:27]C=1)N(C)C=C2CCO.[N:35]([CH2:38][CH2:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([F:57])[C:47]=2[O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[NH:42][CH:41]=1)=[N+:36]=[N-:37]>>[N:35]([CH2:38][CH2:39][C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([F:57])[C:47]=2[O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:42]([CH2:20][CH:21]2[CH2:22][CH2:26][CH2:27][CH2:34][O:33]2)[CH:41]=1)=[N+:36]=[N-:37]

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 58303904HCID 58303904, compoundHCID 58304038HCID 58304038, compound

Product 1

HCID 58303876HCID 58303876, compoundYield 82%

Procedure

Following the procedure (step 5, scheme 17, TBAF deprotection step unnecessary) used to prepare compound 17-6, compound 19-1 gave compound 19-2 in 82% yield as a colorless oil. 1H NMR (CDCl3, 300 MHz) (ppm): 7.25-7.47 (m, 5H), 6.91-6.97 (m, 3H), 3.91-4.04 (m, 3H), 3.58 (m, 1H), 3.36-3.43 (m, 3H), 2.97 (t, J=6.9 Hz, 2H), 1.23-1.48 (m, 6H).

Sources & evidence

ORD record
ord-d5f481c5387f449b994568df30af1997
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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