Tetrahydrofuran → Methyl 2'-fluoro-4-(hydroxymethyl)-5'-(methyloxy)-1,1'-biphenyl-2-carboxylate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16](O)=[O:17])=[CH:12][C:11]=1[C:19]([O:21][CH3:22])=[O:20].C1COCC1.B.C1COCC1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:19]([O:21][CH3:22])=[O:20])=[CH:12][C:13]([CH2:16][OH:17])=[CH:14][CH:15]=1Participants
4
Conditions
- Temperature
- 23 °C
Procedure
To a stirred solution of 2′-fluoro-5′-(methyloxy)-2-((methyloxy)carbonyl)-1,1′-biphenyl-4-carboxylic acid T4.3 (35.60 g, 117 mmol) in THF (1170 mL, 117 mmol) at 0° C. was added borane-THF (234 mL, 234 mmol). The reaction was warmed to 23° C., and the mixture was stirred for 6 hours. The mixture was then concentrated in vacuo. 1 N HCl was added, and the mixture was extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified on silica gel (0-40% EtOAc in hexane) to give methyl 2′-fluoro-4-(hydroxymethyl)-5′-(methyloxy)-1,1′-biphenyl-2-carboxylate T4.4 as a clear oil (30.00 g, 88% yield). MS ESI (pos.) m/e: 308.0 (M+H2O)+, 291.1 (M+H)+.