Tetrabutylammonium Fluoride → HCID 67418199, compound

HRID 2035400Notes

Reaction equation

HRID 2035400 reaction equation
C([Si]([O:18][CH2:19][C:20]1[CH:25]=[C:24]([C@H:26]2[C@@H:31]([O:32][CH2:33][O:34][CH3:35])[C@@H:30]([O:36][CH2:37][O:38][CH3:39])[C@H:29]([O:40][CH2:41][O:42][CH3:43])[CH:28]([CH2:44][O:45][CH2:46][O:47][CH3:48])[O:27]2)[CH:23]=[CH:22][C:21]=1[Cl:49])(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:49][C:21]1[CH:22]=[CH:23][C:24]([C@H:26]2[C@@H:31]([O:32][CH2:33][O:34][CH3:35])[C@H:30]([O:36][CH2:37][O:38][CH3:39])[C@H:29]([O:40][CH2:41][O:42][CH3:43])[CH:28]([CH2:44][O:45][CH2:46][O:47][CH3:48])[O:27]2)=[CH:25][C:20]=1[CH2:19][OH:18]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67417361HCID 67417361, compound

Product 1

HCID 67418199HCID 67418199, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product from step A (1.3 g, 1.8 mmol) in tetrahydrofuran (16 mL) at 0° C. was added dropwise tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran; 2.2 mL, 2.2 mmol). The reaction mixture was warmed to room temperature and stirred for 4 h. Then it was concentrated and the crude material obtained was purified by flash column chromatography (eluent: hexanes/ethyl acetate 100:0 to 75:25) to give compound (2-chloro-5-((2S,3R,4S,5R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol (0.81 g, 94%) as a colorless syrup: 1H NMR (CDCl3, 500 MHz) δ 7.54 (br d, J=2.0 Hz, 1H), 7.33 (d, J=8.2 Hz, 1H), 7.28 (dd, J=8.2, 2.0 Hz, 1H), 4.91 (d, J=6.4 Hz, 1H), 4.89 (d, J=6.3 Hz, 1H), 4.87 (d, J=6.3 Hz, 1H), 4.78-4.76 (m, 3H), 4.65 (s, 2H), 4.47 (d, J=6.5 Hz, 1H), 4.19 (d, J=9.5 Hz, 1H), 4.14-4.10 (m, 2H), 3.92 (dd, J=11.3, 1.6 Hz, 1H), 3.76 (t, J=8.8 Hz, 1H), 3.71 (dd, J=11.2, 5.2 Hz, 1H), 3.63-3.58 (m, 2H), 3.53 (t, J=9.4 Hz, 1H), 3.452 (s, 3H), 3.448 (s, 3H), 3.34 (s, 3H), 2.82 (s, 3H); ESI MS m/z 481 [M+H]+.

Workup

  1. concentrationThen it was concentrated
  2. customthe crude material obtained
  3. customwas purified by flash column chromatography (eluent: hexanes/ethyl acetate 100:0 to 75:25)

Sources & evidence

ORD record
ord-cd53ce904de0430ab3579220bd656db0
Source dataset
uspto-grants-2013_11
Patent number
US08575114B2

Reaction notes

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