Nitrogen → HCID 58386120, compound

HRID 1963025Notes

Reaction equation

HRID 1963025 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH:7]([OH:9])[CH3:8].[CH3:17][Si:18]([CH2:21][CH2:22][O:23][CH2:24]Cl)([CH3:20])[CH3:19].CCN(C(C)C)C(C)C.N#N>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:4]=1[O:5][CH2:6][CH:7]([O:9][CH2:24][O:23][CH2:22][CH2:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH3:8]

Participants

6

Reactant 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 58858087HCID 58858087, compound

Product 1

HCID 58386120HCID 58386120, compoundYield 156.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(2-methoxy-4-nitrophenoxy)propan-2-ol (1.537 g, 6.76 mmol) in DCM (20 mL) was added SEM-Cl (2.4 mL, 13.5 mmol) followed by DIPEA (4.7 mL, 27.1 mmol) dropwise under N2. The mixture was stirred O.N. at RT., diluted with DCM (20 mL), washed with 1N HCl, brine, dried (Na2SO4), and evaporated under reduced pressure to obtain a yellow oil (3.79 g) which was purified by flash chromatography (40 g silica, 0% to 100% EtOAc-Hexanes) to yield. Example 6A (2.03 g, 5.68 mmol, 84% yield) as a yellow oil.

Workup

  1. customat RT
  2. washwashed with 1N HCl, brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0f48fc01dbfa4070aba33d1a6f887102
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

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