Ethanol → HCID 53356865, compound

HRID 877487Notes

Reaction equation

[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([CH3:25])[C:8]([C:21]([F:24])([F:23])[F:22])([O:16][Si](C)(C)C)[C:9]=1[NH:10]2.[OH-].[K+].CCO>C1COCC1.O>[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([CH3:25])[C:8]([C:21]([F:22])([F:23])[F:24])([OH:16])[C:9]=1[NH:10]2

Participants

Conditions

Temperature: 60 °C

Procedure

5,6-Dichloro-2-methyl-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.15 g, 0.3 mmol) was dissolved in THF (5 mL) and a solution of KOH (0.068 g, 1.2 mmol) in water (5 mL) was added followed by EtOH (2 mL). The reaction mixture was heated at 60° C. for 6 h, diluted with water (10 mL) and extracted into EtOAc (2×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude residue which was purified by column chromatography [EtOAc-hexane (1:4) as eluant] to provide the title compound (0.02 g, 20%). 1H NMR (500 MHz, CDCl3, δ in ppm) (mixture of two diastereomers) 8.35 (br s, 1H), 8.28 (br s, 1H), 7.26 (d, J=8.5 Hz, 2H), 7.19 (d, J=8 Hz, 2H), 3.26-2.98 (m, 4H), 2.51 (s, 1H), 2.46-2.42 (m, 1H), 2.35 (s, 1H), 2.26 (m, 1H), 2.12-1.97 (m, 3H), 1.84-1.78 (m, 1H), 1.21-1.18 (m, 5H).

Workup

extractionextracted into EtOAc (2×50 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated under reduced pressure
customto give the crude residue which
customwas purified by column chromatography [EtOAc-hexane (1:4) as eluant]

Sources & evidence

ORD record: ord-b24dc3b378a2446eb2e08b0df73165e5
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987319B2

Reaction notes

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