Tetrahydrofuran → HCID 25114168, compound

HRID 1930758Notes

Reaction equation

HRID 1930758 reaction equation
O1CCCC1.[CH2:6]([Sn:10]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:13][CH2:14][CH2:15][CH3:16])[C:11]#[CH:12])[CH2:7][CH2:8][CH3:9].[N+:21]([CH2:24][CH2:25][C:26]1[CH:39]=[CH:38][C:29]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:28][CH:27]=1)([O-:23])=O.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CN(C)C1C=CN=CC=1.O.C(OCC)(=O)C>[CH2:17]([Sn:10]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:6][CH2:7][CH2:8][CH3:9])[C:11]1[O:23][N:21]=[C:24]([CH2:25][C:26]2[CH:39]=[CH:38][C:29]([CH2:30][O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[CH:28][CH:27]=2)[CH:12]=1)[CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 90495Di-tert-butyl dicarbonateHCID 621176EthynyltributyltinHCID 580762662-((4-(2-Nitroethyl)benzyl)oxy)pyridine

Product 1

HCID 25114168HCID 25114168, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (90 mL) of tri-n-butylethynyl tin (3 g), the 2-(4-(2-nitro-ethyl)-benzyloxy)-pyridine (4.9 g) described in Manufacturing Example 1-1-4 and 4-dimethylaminopyridine (116 mg) was added a tetrahydrofuran solution (30 mL) of di-tert-butyl dicarbonate (7.3 g), which was stirred at room temperature for 15 hours. Ethyl acetate and water were added to the mixture. The organic layer was isolated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was adsorbed on silica gel, and purified by silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain the title compound (5.3 g).

Workup

  1. customThe organic layer was isolated
  2. washwashed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. custompurified by silica gel column chromatography (heptane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-369247a5a36f479ea135161ccd8ccd93
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

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