Methanol → 3-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid

HRID 1354503Notes

Reaction equation

HRID 1354503 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.CO.[C:15]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C[O-].[Na+]>O>[C:15]1([C:3]2[C:4]3[C:9](=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7967CyclohexanoneHCID 5952301H-indole-6-carboxylic acidHCID 10942334Sodium Methoxide

Product 1

HCID 111840773-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 12 L round-bottomed flask was equipped with a reflux condenser and a mechanical stirrer, and the system was purged with nitrogen gas. 6-indole carboxylic acid (300.00 g, 1.86 mole, 3 equivalents) was charged into the flask, followed by MeOH (5.5 L). After stirring for 10 min at room temperature, cyclohexanone (579 mL, 5.58 mole) was added. Methanolic sodium methoxide (25% w/w, 2.6 L, 11.37 mole, 6.1 equivalents) was added in portions over 10 min. The mixture was then refluxed for 48 h. After cooling to room temperature, water (4 L) was added and methanol removed under reduced pressure. The residual aqueous phase was acidified to pH 1 with concentrated HCl (˜1.2 L). The resulting yellowish precipitate was collected by filtration, washed with water and dried under vacuum at 50° C. The desired cyclohexene derivative was obtained as a beige solid (451.0 g, 100% yield).

Workup

  1. customA 12 L round-bottomed flask was equipped with a reflux condenser and a mechanical stirrer
  2. customthe system was purged with nitrogen gas
  3. temperatureThe mixture was then refluxed for 48 h
  4. temperatureAfter cooling to room temperature
  5. custommethanol removed under reduced pressure
  6. filtrationThe resulting yellowish precipitate was collected by filtration
  7. washwashed with water
  8. customdried under vacuum at 50° C

Sources & evidence

ORD record
ord-66864b8fa80244b2b5bd2f103368073a
Source dataset
uspto-grants-2007_05
Patent number
US07223785B2

Reaction notes

Loading…