2-Nitrophenol → 7-(Diphenylmethoxy)-1H-indole

HRID 1198561Notes

Reaction equation

HRID 1198561 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-])=O.[CH:11]([Mg]Br)=[CH2:12].[Cl-].[NH4+].[CH2:17]1[CH2:21]O[CH2:19][CH2:18]1>>[CH:17]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[NH:1][CH:12]=[CH:11]2)([C:21]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1)[C:18]1[CH:19]=[CH:18][CH:17]=[CH:21][CH:19]=1

Participants

5

Reactant 4

HCID 69472-NitrophenolHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 150540087-(Diphenylmethoxy)-1H-indole

Conditions

Temperature
-40 °C

Procedure

To a stirred solution of the protected nitrophenol (3.05 g, 10 mmol) (Example 34a part i) in dry THF (100 ml) at -40° C. under nitrogen was added 1M vinyl magnesium bromide in the THF (35 ml) over 5 minutes. After stirring for a further three quarters of an hour at -40° C., the reaction mixture was poured into aqueous ammonium chloride and extracted into diethyl ether. The combined organic extracts were dried, filtered and evaporated in vacuo. The product was purified by column chromatography on silica, eluting with 12.5% ethyl acetate in hexane, to give a pale yellow solid.

Workup

  1. extractionextracted into diethyl ether
  2. customThe combined organic extracts were dried
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe product was purified by column chromatography on silica
  6. washeluting with 12.5% ethyl acetate in hexane
  7. customto give a pale yellow solid

Sources & evidence

ORD record
ord-4c30f4a8a9dc44fe89bf85f0c7b47a29
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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