Thiazole → 7-Phenyl-1-(thiazol-2-yl)-heptan-1-ol

HRID 877405Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]C(C)(C)C.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1.CCOC(C)=O>[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[OH:24])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Thiazole (21 μL, 0.29 mmol) in anhydrous THF (1.9 mL) was cooled to −78° C. and treated dropwise with 1.4 M t-BuLi (273 μL, 0.38 mmol). The reaction mixture was stirred at −78° C. for 0.5 h before a solution of 7-phenylheptanal (73 mg, 0.38 mmol) in THF (1.3 mL) was added. The reaction mixture was stirred at −78° C. for 0.5 h before being warmed to room temperature. The reaction mixture was diluted with EtOAc, and washed with H2O, saturated aqueous NaHCO3 and saturated aqueous NaCl before the organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. Flash chromatography (SiO2, 1.5×6.5 cm, 15-25% EtOAc-hexanes) afforded the title compound (50 mg, 62%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.68 (d, 1H, J=3.2 Hz), 7.24 (m, 3H), 7.14 (m, 3H), 4.96 (dd, 1H, J=4.8, 7.6 Hz), 3.09 (br s, 1H), 2.56 (t, 2H, J=7.8 Hz), 1.87 (m, 2H), 1.58 (m, 2H), 1.44 (m, 6H).

Workup

additionwas added
temperaturebefore being warmed to room temperature
washwashed with H2O, saturated aqueous NaHCO3 and saturated aqueous NaCl before the organic layer
dry with materialwas dried over Na2SO4
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-22c9ac5fc43d4225bb35b0a924152e94
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987312B2

Reaction notes

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