Benzyl Alcohol → benzyl 1H-indole-2-carboxylate

HRID 982027Notes

Reaction equation

HRID 982027 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].[CH2:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 72899Indole-2-carboxylic acid

Product 1

HCID 7723355benzyl 1H-indole-2-carboxylateYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 19.9 g (124 mmol) of indole-2-carboxylic acid, 16 ml (155 mmol) of benzyl alcohol, and 3.0 g (25 mmol) of 4-dimethylaminopyridine in 800 ml of dichloromethane was treated with 25.6 g (124 mmol) of N,N'-dicyclohexylcarbodiimide and stirred at ambient temperature for 2.5 h. The resulting mixture was filtered, concentrated in vacuo, taken up in 1 l of ethyl acetate, and filtered. The solution was subsequently washed sequentially with 1N NCl, H2O, saturated NaHCO3, and saturated brine, dried over MgSO4, and concentrated. Recrystallization of the residue from ethyl acetate/hexane gave three crops of crystalline material containing 15.79 g, 11.13 g, and 2.25 g of the desired compound (94%). 1H NMR (CDCl3) δ 5.40 (s,2H), 7.26 (br t,1H), 7.3-7.5 (m,8H), 7.69 (br d,1H), 8.9 (br s,1H). Mass spectrum: (M+H)+ =252.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered
  4. washThe solution was subsequently washed sequentially with 1N NCl, H2O, saturated NaHCO3, and saturated brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customRecrystallization of the residue from ethyl acetate/hexane
  8. customgave three crops of crystalline material

Sources & evidence

ORD record
ord-c27216f9498145bf8b3c32f3a31cb9e0
Source dataset
uspto-grants-1991_02
Patent number
US04994477

Reaction notes

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