Water → HCID 68495565, compound

HRID 1944206Notes

Reaction equation

HRID 1944206 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][C:8]([CH3:23])([CH3:22])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[CH2:10]2)=[CH:5][C:4]=1[O:24][Si](C(C)C)(C(C)C)C(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[CH3:21][O:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][N:9]1[C:8]([CH3:23])([CH3:22])[CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([OH:24])[CH:5]=2)[CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 68497112HCID 68497112, compound

Product 1

HCID 68495565HCID 68495565, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 226 (237 mg, 0.45 mmol) in THF (10 ml) at 0° C. (ice-bath) was added TBAF (1.0 M in THF, 0.53 ml, 0.53 mmol). The reaction mixture was stirred at 0° C. for 18 h. water (10 ml) was added and the aqueous layer was extracted with EtOAc (3×). The combined organic layer were washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo. Purification (flashmaster: 20 g, 100% hex to 100% EtOAc over 25 min) afforded the title compound (70 mg, 43%) as a colourless oil. 1H NMR (270 MHz; CDCl3) 1.18 (6H, s, 2×CH3), 2.66 (2H, s, CH2), 3.50 (2H, s, CH2), 3.65 (2H, s, CH2), 3.79 (3H, s, OCH3), 3.83 (3H, s, OCH3), 6.47 (1H, s, CH), 6.52 (1H, s, CH), 6.75-6.79 (1H, m, CH), 6.95-6.97 (2H, m, 2×CH), 7.21 (1H, t, J=8.0 Hz, CH). 13C NMR (100 MHz; CDCl3) 23.72 (CH3), 45.54 (CH2), 49.97 (CH2), 52.49 (C), 53.45 (CH2), 55.13 (OCH3), 55.86 (OCH3), 110.69 (CH), 111.73 (CH), 111.90 (CH), 114.09 (CH), 120.88 (CH), 125.60 (C), 126.86 (C), 129.11 (C), 142.41 (C), 143.49 (C), 144.99 (C), 159.59 (C). LC/MS (ES−) tr=1.85 min, m/z 326.27 (M−H)−. HRMS (ES+) calcd. for C20H26NO3 (M++H) 328.1907, found 328.1904.

Workup

  1. additionwas added
  2. extractionthe aqueous layer was extracted with EtOAc (3×)
  3. washThe combined organic layer were washed with brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification (flashmaster: 20 g, 100% hex to 100% EtOAc over 25 min)

Sources & evidence

ORD record
ord-efb093c59db14ade93069ed0bdac2c78
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

Loading…