C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:8]([O:19][CH2:20][CH3:21])[CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C.Cl>C1COCC1>[CH2:20]([O:19][C:8]1[CH:7]=[C:6]([CH2:4][OH:3])[CH:11]=[CH:10][C:9]=1[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[CH3:21]To a solution of 2-ethoxy-4′-fluoro-biphenyl-4-carboxylic acid ethyl ester (0.50 g, 1.73 mmol, 1.0 equiv) in anhydrous THF (10 mL) was added slowly over a time period of 15 min under cooling to −10° C. a solution of diisobutylaluminium hydride (5.2 mL, 5.20 mmol, 3.0 equiv; 1 M solution in hexane). After 1 h, the reaction mixture was poured on ice, the pH adjusted to 4 by addition of a 1 M solution of HCl, the solution extracted with ethyl acetate (2×100 mL) and the combined organic phases washed with water (2×100 mL) and a conc. solution of sodium chloride (100 mL). The organic phase was dried over MgSO4, concentrated by evaporation under reduced pressure to give 0.42 g (99%) of the title compound which was directly used in the consecutive step without further purification.
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