Tetrahydrofuran → {6-[(5-Methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methanol

HRID 2221528Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:33]=[CH:32][C:18]2[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:20]([C:22](OC)=[O:23])[O:21][C:17]=2[CH:16]=1.O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:33]=[CH:32][C:18]2[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:20]([CH2:22][OH:23])[O:21][C:17]=2[CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of methyl 6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-carboxylate (32.70 g) and tetrahydrofuran (500 mL) was added dropwise diisobutylaluminum hydride (0.95M hexane solution, 235 mL) at 0° C. The reaction mixture was stirred at 0° C. for 2 hrs, sodium sulfate decahydrate (71.85 g) was added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate and the precipitate was filtered off. The filtrate was concentrated to give {6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methanol as colorless crystals (27.80 g, yield 91%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 152-153° C.

Workup

stirringthe mixture was stirred at room temperature for 30 min
filtrationthe precipitate was filtered off
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-48eacb6dc0624bcfb3d3467f721cbc3f
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368578B2

Reaction notes

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