Dichloromethane → HCID 86609321, compound

HRID 2265769Notes

Reaction equation

HRID 2265769 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-:18].[C:19]([O:23][C:24]([N:26]([CH3:52])[C:27]1[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]2[CH:51]=[CH:50][C:38]([O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44]OS(C)(=O)=O)=[CH:37][CH:36]=2)=[CH:29][CH:28]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20].ClCCl>C1COCC1>[C:19]([O:23][C:24](=[O:25])[N:26]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]2[CH:51]=[CH:50][C:38]([O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][F:18])=[CH:37][CH:36]=2)=[CH:29][CH:28]=1)[CH3:52])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 86609322HCID 86609322, compound

Product 1

HCID 86609321HCID 86609321, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous TBAF (Cox D P, et al., J Org Chem. 1984; 49:3216-19) (38.5 mg 0.15 mmol) was added to a solution of compound 10a (14.5 mg, 0.03 mmol) in anhydrous THF (3 ml). The mixture was refluxed for 4 hours. After cooled to room temperature, standard workup with dichloromethane was applied and the residue was purified by silica gel preparative TLC (2% methanol in dichloromethane) to afford compound 11a (7 mg, 57%): 1H NMR δ 7.43 (d, 4H, J=8.6 Hz), 7.20 (d, 2H, J=8.4 Hz), 6.97 (q, 2H), 6.91 (d, 2H, J=8.6 Hz), 4.60 (d, t, 2H, J1=47 Hz, J2=4.0 Hz), 4.17 (t, 2H), 3.90 (t, 3H), 3.75 (t, 1H), 3.27 (s, 3H), 1.46 (s, 9H).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customthe residue was purified by silica gel preparative TLC (2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-bd5269f682cd472f86fb3327f8c67d2d
Source dataset
uspto-grants-2010_12
Patent number
US07858072B2

Reaction notes

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