Tetrahydrofuran → HCID 68486336, compound

HRID 1875115Notes

Reaction equation

HRID 1875115 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:10]([CH3:12])[CH3:11])[NH:5][C:6]=1[C:7]([O-:9])=[O:8].[H-].[Na+].Cl[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21].C(=O)(O)[O-].[Na+].[CH2:29]1COC[CH2:30]1>C(Cl)Cl>[CH3:1][C:2]1[N:3]=[C:4]([CH:10]([CH3:12])[CH3:11])[N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[C:7]([O:9][CH2:29][CH3:30])=[O:8]

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178432757HCID 178432757, compound

Product 1

HCID 68486336HCID 68486336, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-methyl-2-(1-methylethyl)-1H-imidazole-5-carboxylate (83 mg, 0.42 mmol) in THF (2.0 mL) was added dropwise to a suspension of NaH (60% in oil, 19.2 mg, 0.47 mmol) in THF (3.0 mL) at 0° C. under N2. The mixture was allowed warm up to room temperature and stirred for 2 h, it was then cooled to 0° C. and {2-[(chloromethyl)oxy]ethyl}(trimethyl)silane (84 uL, 0.47 mmol) was added dropwise. The mixture was stirred overnight at room temperature and saturated sodium bicarbonate was added. DCM was added and the organic layer was dried over sodium sulfate and concentrated. The residue was purified by column chromatography (0-2% 2M NH3 solution of MeOH in DCM) to give the title compound (133 mg, 96%) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.16 (2H, s) 4.34 (2H, q, J=7.1 Hz) 3.44-3.51 (2H, m) 3.06 (1H, dt, J=13.8, 6.9 Hz) 2.54 (3H, s) 1.30-1.39 (9H, m) 0.84-0.92 (2H, m) −0.07-−0.02 (9H, m). LCMS: m/z 327 (M+1).

Workup

  1. temperatureit was then cooled to 0° C.
  2. stirringThe mixture was stirred overnight at room temperature
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (0-2% 2M NH3 solution of MeOH in DCM)

Sources & evidence

ORD record
ord-d155d67ea49545ffb41dfd59fbcff4b1
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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