Tetrabutylammonium Fluoride → HCID 88522873, compound

HRID 2165145Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([N:14]3[C:18](=[O:19])[CH2:17][CH2:16][C:15]3=[O:20])[CH2:11][C:10]([CH3:22])([CH3:21])[C:9]=2/[CH:23]=[CH:24]/[C@@H:25]2[O:30][C:29](=[O:31])[CH2:28][C@@H:27]([O:32][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:26]2)=[CH:4][C:3]=1[CH3:50].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([N:14]3[C:15](=[O:20])[CH2:16][CH2:17][C:18]3=[O:19])[CH2:11][C:10]([CH3:21])([CH3:22])[C:9]=2/[CH:23]=[CH:24]/[C@@H:25]2[O:30][C:29](=[O:31])[CH2:28][C@@H:27]([OH:32])[CH2:26]2)=[CH:4][C:3]=1[CH3:50]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 88495747HCID 88495747, compound

Product 1

HCID 88522873HCID 88522873, compoundYield 597.6%

Procedure

In a manner similar to scheme V, 42 (0.13 gm) was treated with tetrabutylammonium fluoride and the product was purified by SiO2 with 1.5:1 EtOAc:hexanes as the eluent. Concentration in vacuo of the product rich fractions provided 0.51 gm of the product. mp 71°-77° C. Anal. C26H30FNO5 500 0.25 H2 0: Theory C: 67.89; H: 6.68; N: 3.04. Found C: 67.83; H: 6.95; N: 2.90.

Workup

customthe product was purified by SiO2 with 1.5:1 EtOAc
concentrationConcentration in vacuo of the product rich fractions

Sources & evidence

ORD record: ord-bdeff5c55bae4e81b96d1a2870440d06
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04939143

Reaction notes

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