Indole-4-carboxaldehyde → HCID 54527042, compound

HRID 1906189Notes

Reaction equation

HRID 1906189 reaction equation
[Br-].[OH:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.C([Li])CCC.[CH:34]([C:36]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:37]=1[CH:38]=[CH:39][NH:40]2)=O>O1CCCC1.CCCCCC>[NH:40]1[C:41]2[C:37](=[C:36]([CH:34]=[CH:7][C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:28][CH:27]=3)[CH:44]=[CH:43][CH:42]=2)[CH:38]=[CH:39]1

Participants

6

Reactant 3

HCID 333703Indole-4-carboxaldehydeHCID 20212892HCID 20212892, compoundHCID 178418339Butyllithium

Product 1

HCID 54527042HCID 54527042, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

31 g of p-hydroxybenzyltriphenylphosphonium bromide ware suspended in 350 ml of tetrahydrofuran under an inert atmosphere, and over one hour 86 ml of a 1.6 M solution of butyllithium in hexane were added thereto. After stirring for 30 minutes, a solution of 5 g of 4-formyl-indole in 100 ml of tetrahydrofuran was added over 30 minutes, and the mixture was stirred for 24 hours. After dilution with 500 ml of water, the mixture was extracted with ethyl acetate. The fractions with an Rf=0.15 were isolated by chromatography on silica (eluent:methylene chloride) were triturated with petroleum ether (b.p. 60°-80° C.), filtered and dried under reduced pressure to obtain 7 g of 4-[(1H-indol-4-yl)-ethenyl]-phenol melting at ≃145° C.

Workup

  1. stirringthe mixture was stirred for 24 hours
  2. extractionAfter dilution with 500 ml of water, the mixture was extracted with ethyl acetate
  3. customThe fractions with an Rf=0.15 were isolated by chromatography on silica (eluent:methylene chloride)
  4. customwere triturated with petroleum ether (b.p. 60°-80° C.)
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-be2d485089314a9fb444d2ca29303be8
Source dataset
uspto-grants-1987_03
Patent number
US04650811

Reaction notes

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