Propylene Oxide → HCID 22612707, compound

HRID 844196Notes

Reaction equation

HRID 844196 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.[CH2:13]1[O:16][CH:14]1[CH3:15]>O1CCCC1>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:13][CH:14]([OH:16])[CH3:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 24758Sodium hydrideHCID 871116-Chloroindole

Product 1

HCID 22612707HCID 22612707, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of sodium hydride (60%, 1.26 g, 31.6 mmol) in tetrahydrofuran (30 mL) at 0° C. under Ar was added dropwise a solution of 6-chloroindole (4.0 g, 26 mmol) in tetrahydrofuran (30 mL). The mixture was stirred for 1 h and (RS)-propylene oxide (3.7 mL, 53 mmol) was added. The mixture was warmed to room temperature, stirred for 48 h and partitioned between aqueous ammonium chloride solution (100 mL) and ether (3×100 mL). The combined organic extracts were washed with brine (2×100 mL), dried (magnesium sulfate), concentrated in vacuo and purified by column chromatography [SiO2; ethyl acetate-hexane (1:9)] to give the product (2.78 g, 50% yield) as a pale yellow oil. Data for the compounds produced using General Method A, step (a) are listed in Table 3.

Workup

  1. stirringstirred for 48 h
  2. custompartitioned between aqueous ammonium chloride solution (100 mL) and ether (3×100 mL)
  3. washThe combined organic extracts were washed with brine (2×100 mL)
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography [SiO2; ethyl acetate-hexane (1:9)]

Sources & evidence

ORD record
ord-e2cebe5795ab4281810ae323eaa8b296
Source dataset
uspto-grants-2002_04
Patent number
US06380238B1

Reaction notes

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