Potassium Hydroxide → [4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetic acid

HRID 731047Notes

Reaction equation

HRID 731047 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:17]4[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=4[C:23]=3[CH:24]=2)=[CH:8][CH:7]=1.[OH-].[K+]>C1COCC1.CO>[CH2:25]([N:16]1[C:15]2[CH:14]=[CH:13][C:12]([C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:32])=[O:2])=[CH:11][CH:10]=3)=[CH:24][C:23]=2[C:22]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68814354[4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetic acid methyl ester

Product 1

HCID 68813927[4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetic acid

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-(9-benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetic acid methyl ester (0.355 g, 0.834 mmol) was reacted with 1N KOH (1.7 ml) in THF/MeOH (6 ml/4 ml) to give the product (0.261 g, 0.634 mmol, 74%) as a pale-yellow solid, mp 176-180° C. 1H NMR (DMSO-d6) δ 1.77-1.86 (m, 4H), 2.65 (t, J=5.3 Hz, 2H), 2.70 (t, J=6.0 Hz, 2H), 4.69 (s, 2H), 5.33 (s, 2H), 6.96 (d, J=8.7 Hz, 2H), 7.03 (d, J=7.3 Hz, 2H), 7.21 (t, J=7.2 Hz, 1H), 7.25-7.30 (m, 3H), 7.39 (d, J=8.6 Hz, 1H), 7.56 (d, J=8.7 Hz, 2H), 7.58 (d, J=1.7 Hz, 1H), 13.00 (broad s, 1H); IR (solid) 3020, 2920, 1740, 1520, 1470, and 1240 cm−1; [ESI(−)], rn/z 410 (M−H)−; Anal. Calcd. for C27H25NO3: C, 78.81; H, 6.12; N, 3.40; Found: C, 78.69; H, 6.21; N, 3.20.

Sources & evidence

ORD record
ord-81f7ef9e13ff45c3bfc7bad0dd394059
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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