Tetrabutylammonium Fluoride → HCID 67157672, compound

HRID 901776Notes

Reaction equation

HRID 901776 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[O:19][CH:14]([O:15][CH2:16][CH:17]=[CH2:18])[C@H:13]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:12]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:11]1[O:36][C@@H:37]1[O:66][C@H:65]([CH2:67][O:68][Si](C(C)(C)C)(C)C)[C@@H:56]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@H:38]1[O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:21]([O:20][C@@H:13]1[C@@H:12]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:11]([O:36][C@@H:37]2[O:66][C@H:65]([CH2:67][OH:68])[C@@H:56]([O:57][CH2:58][C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C@H:47]([O:48][CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[C@H:38]2[O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@@H:10]([CH2:9][OH:8])[O:19][CH:14]1[O:15][CH2:16][CH:17]=[CH2:18])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 87290346HCID 87290346, compound

Product 1

HCID 67157672HCID 67157672, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The compound (8.67 g, 8.17 mmol) synthesized in Example 5 (5a) was dissolved in tetrahydrofuran (150 mL) and a solution of 1.0 M tetrabutyl ammonium fluoride in THF (20 mL, 20 mmol) was added thereto, followed by stirring of the mixture at room temperature for 5 hours. After the solvent was distilled off under reduced pressure, the residue was purified using silica gel flash column chromatography (methylene chloride:methanol, 50:1, V/V) to obtain the desired title compound (4.19 g, yield 62%) as a colorless oil.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. customthe residue was purified

Sources & evidence

ORD record
ord-aa19c392cdf9414593054694c693e2f8
Source dataset
uspto-grants-2008_04
Patent number
US07361744B2

Reaction notes

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