Water → Methyl Benzoate

HRID 1409975Notes

Reaction equation

HRID 1409975 reaction equation
N1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](CO)=C1.C(N(CC)CC)C.[C:19](Cl)(=[O:26])C1C=CC=CC=1.[OH2:28]>CN(C1C=CN=CC=1)C>[C:3]([O:26][CH3:19])(=[O:28])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3712Indole-3-carbinolHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 7150Methyl BenzoateYield 42%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
0 °C

Procedure

To an oven dried flask that cooled under argon was added the (1H-indol-3-yl)methanol (1.0 grams, 6.8 mmol, 0.1M in dry dichloromethane, purchased from Fisher Scientific, stored over 4 angstrom molecular sieves) and DMAP (0.083 grams, 0.68 mmol). While stirring at 0° C., triethyl amine (2.0 mL, 14.3 mmol, purchased from Fisher Scientific) was added followed by benzoyl chloride (0.96 mL, 8.2 mmol, purchased from Fisher Scientific). Once the reaction was complete it was diluted with water, and the organic layer removed. The aqueous layer was then washed with dichloromethane twice and the organic material combined. The organic material was dried with sodium sulfate, filtered, and concentrated. Purification using a Teledyne ISCO on silica support (hexanes/ethyl acetate gradient) afforded the desired 1-benzoyl-1H-indol-3-yl)methyl benzoate. 42% yield. 1H-NMR δ8.42 (d, 1H), 8.02 (dd, 2H), 7.76 (m, 3H), 7.62 (dd, 1H), 7.54 (m, 3H), 7.47-7.37 (m, 5H), 5.50 (s, 2H).

Workup

  1. customTo an oven dried flask
  2. temperaturethat cooled under argon
  3. customthe organic layer removed
  4. washThe aqueous layer was then washed with dichloromethane twice
  5. dry with materialThe organic material was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification

Sources & evidence

ORD record
ord-9601c6745534443889f42547cd09b6c9
Source dataset
uspto-grants-2014_12
Patent number
US08921401B2

Reaction notes

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