Tetrabutylammonium Fluoride → HCID 71140750, compound

HRID 1468855Notes

Reaction equation

HRID 1468855 reaction equation
[Br:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][O:7][C@H:8]([C@@H:18]2[CH2:20][C@@H:19]2[CH:21]2[CH2:26][CH2:25][N:24]([C:27]3[N:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][N:28]=3)[CH2:23][CH2:22]2)[CH2:9][O:10][Si](C(C)(C)C)(C)C)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][O:7][C@H:8]([C@@H:18]2[CH2:20][C@@H:19]2[CH:21]2[CH2:22][CH2:23][N:24]([C:27]3[N:28]=[CH:29][C:30]([CH2:33][CH3:34])=[CH:31][N:32]=3)[CH2:25][CH2:26]2)[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86717795HCID 86717795, compound

Product 1

HCID 71140750HCID 71140750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the compound prepared in step E (0.37 g, 0.64 mmol) in THF (3 mL) was added TBAF (0.96 mL of 1.0 M solution in THF, 0.96 mmol). Upon stirring at RT for 1 h, silica gel was added to the reaction mixture and a slurry was prepared, which was purified by column chromatography on silica (elution with 2:1 hexane:ethyl acetate) to yield the desired compound. MS (ESI) m/z 460/462 [M+H]+.

Workup

  1. additionsilica gel was added to the reaction mixture
  2. customa slurry was prepared
  3. customwhich was purified by column chromatography on silica (elution with 2:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-6c70a7c12d204c7880a5e2b59b78e091
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

Loading…