Potassium Hydroxide → HCID 11373710, compound

HRID 731101Notes

Reaction equation

HRID 731101 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:15]3[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:8][CH:7]=1.[OH-].[K+]>C1COCC1.CO>[CH3:21][N:17]1[C:18]2[C:14](=[CH:13][C:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])=[CH:7][CH:8]=3)=[CH:20][CH:19]=2)[C:15]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:16]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68814276HCID 68814276, compound

Product 1

HCID 11373710HCID 11373710, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 4. Thus, [4-(1-methyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenoxy]-acetic acid methyl ester (0.184 g, 0.417 mmol) was reacted with 1N KOH (1.0 ml) in THF/MeOH (3 ml/2 ml) to give the product (0.104 g, 0.243 mmol, 58%) as a white solid, mp 146-148° C. 1H NMR (DMSO-d6) δ 0.73 (t, J=6.8 Hz, 3H), 1.10-1.19 (m, 4H), 1.47-1.54 (m, 2H), 2.62 (t, J=7.4 Hz, 2H), 3.52 (s, 3H), 4.66 (s, 2H), 6.96 (d, J=8.9 Hz, 2H), 7.37-7.46 (m, 5H), 7.51 (t, J=7.0 Hz, 2H), 7.57 (d, J=8.9 Hz, 2H), 7.69 (d, J=1.1 Hz, 1H), 12.96 (broad s, 1H); IR (solid) 3040, 2920, 2860, 1730, 1705, 1605, 1520, 1480, 1430, 1370, and 1230 cm−1; [ESI(−)], m/z 427 (M−H)−; Anal. Calcd. for C28H29NO3.0.25H2O: C, 77.84; H, 6.77; N, 3.24; Found: C, 78.13; H, 6.60; N, 3.19.

Sources & evidence

ORD record
ord-242575b79bed4ca090e7e250d7548177
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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