5-Methoxy-1H-indole-2-carbaldehyde → Benzyl (2E)-3-(5-methoxy-1H-indol-2-yl)-2-propenoate

HRID 11010Notes

Reaction equation

HRID 11010 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][CH:41]=1)[NH:38][C:37]([CH:42]=O)=[CH:36]2>C(Cl)Cl>[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][CH:41]=1)[NH:38][C:37](/[CH:42]=[CH:20]/[C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])=[CH:36]2

Participants

4

Reactant 2

HCID 8264565-Methoxy-1H-indole-2-carbaldehydeHCID 3862746Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetate

Product 1

HCID 11843433Benzyl (2E)-3-(5-methoxy-1H-indol-2-yl)-2-propenoateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl (triphenylphosphoranylidene)acetate (49.2 g, 0.120 mol) was added to a stirred solution of 5-methoxy-1H-indole-2-carbaldehyde (1) (20.0 g, 0.114 mol) in CH2Cl2 (500 mL) and the solution was stirred at room temperature for 4 h. The solvent was removed in vacuo and the residue slurried with methanol (200 mL), whereupon crystallisation of the product occurred. The mixture was filtered, washed with several portions of cold methanol, and dried to give benzyl (2E)-3-(5-methoxy-1H-indol-2-yl)-2-propenoate (2) in a 30.46 g, 87% yield as pale yellow plates; mp 155–157° C. 1H NMR δ (CDCl3) 8.28 (s, 1H), 7.69 (d, J=16.1 Hz, 1H), 7.43–7.32 (m, 5H), 7.23 (d, J=9.1 Hz, 1H), 7.03 (d, J=2.3 Hz, 1H), 6.92 (dd, J=9.1, 2.3 Hz, 1H), 6.74 (d, J=1.8 Hz, 1H), 6.24 (d, J=16.1 Hz, 1H), 5.26 (s, 2H), 3.84 (s, 3H).Found: C, 74.45; H, 5.62; N, 4.58. C19H17NO3 requires C, 74.25; H, 5.57; N, 4.56.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue slurried with methanol (200 mL), whereupon crystallisation of the product
  3. filtrationThe mixture was filtered
  4. washwashed with several portions of cold methanol
  5. customdried

Sources & evidence

ORD record
ord-526f417124d842ee909b2a74f393688d
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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