Tetrabutylammonium Fluoride → HCID 23650647, compound

HRID 1514660Notes

Reaction equation

HRID 1514660 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[C:10]([C:22]2[O:23][C:24]([C:37](C)(C)[O:38][SiH2]C(C)(C)C)=[CH:25][C:26](=[O:36])[C:27]=2[O:28][Si](C(C)(C)C)(C)C)=[CH:9]1)=O)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:28][C:27]1[C:26](=[O:36])[CH:25]=[C:24]([CH2:37][OH:38])[O:23][C:22]=1[C:10]1[C:11]2[C:16](=[C:15]([CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[CH:14]=[CH:13][CH:12]=2)[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131728522HCID 131728522, compound

Product 1

HCID 23650647HCID 23650647, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 204 (200 mg, 0.306 mmol) was dissolved in anhydrous THF (2 mL). TBAF (1M, 4.6 mL) was added dropwise. After stirring for 2 h at room temperature, the solution was brought to reflux for 12 h, then cooled to room temperature and quenched with dilute HCl. The mixture was extracted with EtOAc. The organic phase was combined and washed with water and brine. The organic layer was dried over Na2SO4 then solvent removed under vacuum. After flash column chromatography, the desired product was obtained as a yellow solid (54 mg, 54%). Mp: 201° C. (dec). 1H NMR (CDCl3): δ 1.69 (3H, s), 1.72 (3H, s), 3.75 (2H, d, J=6.6 Hz), 4.61 (2H, s), 5.25 (1H, m), 6.45 (1H, s), 7.2-7.3 (2H, m), 7.85 (1H, m), 8.24 (1H, m). 13C NMR (CDCl3): δ 28.5, 31.4, 33.1, 61.8, 111.3, 119.4, 123.1, 123.9, 126.1, 127.5, 129.1, 129.7, 130.6, 133.7, 134.6, 137.5, 141.1, 149.3, 165.6, 175.9. IR (KBr): 3376, 3148, 2975, 2870, 1611, 1569, 1205, 976 cm−1. HRMS (FAB): m/z Calcd. for C19H19NO4 [M+] 325.1314. found 325.1332.

Workup

  1. temperatureto reflux for 12 h
  2. temperaturecooled to room temperature
  3. customquenched with dilute HCl
  4. extractionThe mixture was extracted with EtOAc
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-4bec765155444ca08f128c1a04c851ef
Source dataset
uspto-grants-2012_07
Patent number
US08222279B2

Reaction notes

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