Potassium Hydroxide → HCID 9842914, compound

HRID 2290144Notes

Reaction equation

HRID 2290144 reaction equation
C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH:27]([CH3:29])[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.C(C1C2OCC(C)(C)C=2C=C(NC(C)C)C=1)(C)(C)C.[OH-].[K+]>C(O)C>[CH:27]([N:11]([C:12]1[CH:13]=[C:14]([C:23]([CH3:25])([CH3:24])[CH3:26])[C:15]2[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=2[CH:22]=1)[C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:30])=[O:3])=[CH:10][CH:9]=1)([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 18699171HCID 18699171, compound2×HCID 53937827HCID 53937827, compound2×

Product 1

HCID 9842914HCID 9842914, compoundYield 3.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following general procedure H and using 4-[isopropyl-(7-t-butyl-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 40, 0.1 5 g contaminated with 67% of 5-(isopropyl)amino-7-t-butyl-3,3-dimethyl-2,3-dihydro-benzofuran (Compound 36) and 2.5 mL of 4M potassium hydroxide solution in 4 mL of ethanol, the title compound (0.034 g, 3.7% for 2 steps) was obtained. 1H NMR (300 MHz, CDCl3): δ 7.86(d, 2H, J=9.0 Hz), 6.75 (d, 1H, J=2.1 Hz), 6.66 (d, 1H, J=2.1 Hz), 6.51 (d, 2H, J=9.1 Hz), 4.36 (heptet, 1H, J=6.5 Hz), 4.28 (s, 2H), 1.34 (s, 9H), 1.32(s, 6H), 1.15 (d, 6H, J=6.5 Hz).

Sources & evidence

ORD record
ord-6d6feef9feb949fab5123a1806f28455
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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