Propylene Oxide → (6-Benzyloxy-indol-1-yl)-propan-2-ol

HRID 2121861

Reaction equation

HRID 2121861 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][NH:17]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:20]1[O:23][CH:21]1[CH3:22].P([O-])(O)(O)=O.[K+]>C1COCC1.C(OCC)(=O)C>[CH2:3]([O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][N:17]2[CH2:20][CH:21]([OH:23])[CH3:22])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6378Propylene Oxide2×HCID 24758Sodium hydrideHCID 2608046-(benzyloxy)-1H-indoleHCID 516951Monobasic potassium phosphate

Product 1

HCID 22247173(6-Benzyloxy-indol-1-yl)-propan-2-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred, cooled (10° C.) suspension of sodium hydride (80.7 g of a 60% dispersion to in mineral oil, 2.02 mol) in anhydrous THF (1.9 L) was added a solution of 6-benzyloxyindole (375 g, 1.68 mol) in anhydrous THF (1.9 L) keeping the temperature below 25° C. After 2 h at 10° C., propylene oxide (140 mL, 2.0 mol) was added dropwise keeping the temperature below 25° C. After 48 h at 10° C., propylene oxide (71 mL, 1.0 mol) was added. After 96 h at 10° C., saturated aqueous potassium dihydrogenphosphate (3.8 L) and ethyl acetate (3.8 L) were carefully added, the layers were separated and the aqueous solution was extracted with 3.8 L of ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to yield a solid (520 g, 110%, contains mineral oil).

Workup

  1. temperatureTo a stirred, cooled
  2. customthe temperature below 25° C
  3. customthe temperature below 25° C
  4. waitAfter 48 h at 10° C.
  5. waitAfter 96 h at 10° C.
  6. customthe layers were separated
  7. extractionthe aqueous solution was extracted with 3.8 L of ethyl acetate
  8. dry with materialThe combined organic extracts were dried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto yield a solid (520 g, 110%, contains mineral oil)

Sources & evidence

ORD record
ord-7c1370929fab4ab5a31e5df4bb32ed59
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Linked notes

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