Propylene Oxide → HCID 22285728, compound

HRID 1061725Notes

Reaction equation

HRID 1061725 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH2:15][CH2:14][CH2:13][C:8]3=[N:9][NH:10][C:11]([CH:12]=1)=[C:7]23)([O-:3])=[O:2].[O-]CC.[Na+].[CH2:20]1[O:23][CH:21]1[CH3:22].[Cl-].[NH4+]>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[CH2:15][CH2:14][CH2:13][C:8]3=[N:9][N:10]([CH2:20][CH:21]([OH:23])[CH3:22])[C:11]([CH:12]=1)=[C:7]23)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 25517Ammonium ChlorideHCID 2723922Sodium ethoxideHCID 178526399HCID 178526399, compound

Product 1

HCID 22285728HCID 22285728, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the product from Step B (4.85 g, 23.9 mmol) in ethanol (50 mL) was added sodium ethoxide (14.2 mL, 35.0 mmol, 21% solution in ethanol) at room temperature. After 30 min, propylene oxide (4.14 mL, 47.8 mmol) was added, and the resultant solution was stirred for 18 h at room temperature. A saturated aqueous ammonium chloride solution (20 mL) was added to the reaction mixture and the ethanol was evaporated. This mixture was extracted with ethyl acetate (3×65 mL) and the combined extracts were washed with brine (30 mL), dried (MgSO4), and evaporated. The residue was purified by column chromatography (silica, 50% to 80% gradient of ethyl acetate in hexane) to yield the desired product as a solid (2.0 g, 32%): m.p: 147-148° C.; MS (ES) m/z 262 (M+); 1H NMR (CDCl3) δ 8.17 (1H, s), 7.74 (1H, s), 4.31 (3H, m), 3.05 (4H, 2d, J=6.0 Hz), 2.19 (4H, m), 1.30 (3H, t, J=6.0 Hz). The regioisomer formed during the alkylation was also isolated as a solid (1.4 g, 22%): mp 140-141° C.

Workup

  1. customthe ethanol was evaporated
  2. extractionThis mixture was extracted with ethyl acetate (3×65 mL)
  3. washthe combined extracts were washed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica, 50% to 80% gradient of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0a44e6aa4a194ded96c7125bca665c04
Source dataset
uspto-grants-2005_11
Patent number
US06960608B2

Reaction notes

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