Acetaldehyde → 1-(4-Chloro-2-phenyl-thieno[3,2-c]pyridin-7-yl)-ethanol

HRID 1268873Notes

Reaction equation

Br[C:2]1[C:3]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][C:4]=2[C:5]([Cl:8])=[N:6][CH:7]=1.C1C=CC=CC=1.[Li]CCCC.[CH:29](=[O:31])[CH3:30]>C1COCC1.CCCCCC>[Cl:8][C:5]1[C:4]2[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[S:11][C:3]=2[C:2]([CH:29]([OH:31])[CH3:30])=[CH:7][N:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

7-bromo-4-chloro-2-phenyl-thieno[3,2-c]pyridine 95 (130 mg, 0.40 mmol) was azeotroped to dryness from benzene and dissolved in THF (11 mL). Upon cooling to −78° C., the solution was treated dropwise with n-BuLi (168 μl of a 2.5 M solution in hexane, 0.42 mmol). After 2 min, acetaldehyde (50 μl, 0.89 mmol) was added and the resultant solution was stirred at −78° C. for 1 h. After this time, the reaction mixture was warmed to 0° C., quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (3×). The organic layers were dried over Na2SO4, filtered, and the filtrate was purified by silica gel column chromatography (eluent: hexane:EtOAc, 4:1) to give 96. 1H NMR (400 MHz, CDCl3) δ: 1.68 (d, J=6.5 Hz, 3H), 2.29 (bd, 1H), 5.22–5.29 (m, 1H), 7.38–7.49 (m, 3H), 7.69 (s, 1H), 7.73–7.78 (m, 2H), 8.13 (s, 1H). MS (EI) m/z (M+H+) 290.

Workup

temperatureAfter this time, the reaction mixture was warmed to 0° C.
customquenched with saturated aqueous ammonium chloride
extractionextracted with ethyl acetate (3×)
dry with materialThe organic layers were dried over Na2SO4
filtrationfiltered
customthe filtrate was purified by silica gel column chromatography (eluent: hexane:EtOAc, 4:1)

Sources & evidence

ORD record: ord-2dd54dd7be894c48b18fa38c2878ef05
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199119B2

Reaction notes

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