Potassium Hydroxide → HCID 9885571, compound

HRID 2290134Notes

Reaction equation

HRID 2290134 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:27][CH3:28])[C:12]2[CH:13]=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:15]3[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=3[CH:22]=2)=[CH:7][CH:6]=1)C.[OH-].[K+]>C(O)C>[CH2:27]([N:11]([C:12]1[CH:13]=[C:14]([C:23]([CH3:24])([CH3:26])[CH3:25])[C:15]2[O:19][CH2:18][C:17]([CH3:20])([CH3:21])[C:16]=2[CH:22]=1)[C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:29])=[O:3])=[CH:10][CH:9]=1)[CH3:28]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54333640HCID 54333640, compound2×

Product 1

HCID 9885571HCID 9885571, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following general procedure H and using 4-[ethyl-(7-t-butyl-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 25, 0.09 g, 0.227 mmol) and 2.5 mL of 4M potassium hydroxide solution in 4 mL of ethanol, the title compound (0.065 g, 78%) was obtained as a pale yellow solid. 1H NMR (300 MHz, CDCl3): δ 7.89 (d, 2H, J=9.0 Hz), 6.87 (d, 1H, J=2.1 Hz), 6.78 (d, 1H, J=2.1 Hz), 6.58 (d, 2H, J=9.2 Hz), 4.28 (s, 2H), 3.74 (q, 2H, J=7.1 Hz), 1.36 (s, 9H), 1.33(s, 6H), 1.27 (t, 3H, J=7.1 Hz).

Sources & evidence

ORD record
ord-c817a78437634c68b5f0e0d2c48f9be5
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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