Tetrabutylammonium Fluoride → HCID 70131253, compound

HRID 1417787Notes

Reaction equation

HRID 1417787 reaction equation
CC([Si](C)(C)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:26]2[CH:25]=[C:24]([C:27](=[O:29])[CH3:28])[CH:23]=[CH:22][C:21]=2[S:20][C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:26]2[CH:25]=[C:24]([C:27](=[O:29])[CH3:28])[CH:23]=[CH:22][C:21]=2[S:20][C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70130690HCID 70130690, compound

Product 1

HCID 70131253HCID 70131253, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 150 mg (0.33 mmol) of 1-[10-[6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]hexyl]-10H-phenothiazin-2-yl]ethanone in 0.6 mL of tetrahydrofuran is treated with 0.41 mL (0.41 mmol) of 1M tetrabutylammonium fluoride in tetrahydrofuran. The reaction is stirred for 3 hours at room temperature, then diluted with 20 mL of ethyl acetate. The organic layer is washed successively with 10% sodium bisulfate solution and saturated sodium chloride solution, then dried over magnesium sulfate and concentrated in vacuo to give 114 mg of 1-[10-(6-hydroxyhexyl)-10H-phenothiazin-2-yl]ethanone as a dark oil. The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 3400, 1680, 1590, 1560 cm-1 ; MS m/e calculated for C20H23NO2S: 341.1449, found 341.1456.

Workup

  1. washThe organic layer is washed successively with 10% sodium bisulfate solution and saturated sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb2c099ab0e64dae9eaab1c28d19a091
Source dataset
uspto-grants-1999_03
Patent number
US05877296

Reaction notes

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