tert-Butyl methyl ether → (2R)-6-Fluoro-3,4-dihydro-2-((2R)-2-oxiranyl)-2H-1-benzopyran

Reaction equation

CC(OC)(C)C.[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C@@H:13]([C@@H:18]1[CH2:20][O:19]1)[CH2:12][CH2:11]2>>[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[O:14][C@@H:13]([C@H:18]1[CH2:20][O:19]1)[CH2:12][CH2:11]2

Participants

Reactant 2

HCID 15413tert-Butyl methyl ether

HCID 20575859(2R, 2'S)-6-Fluoro-2-(2'-oxiranyl)chromane

Product 1

HCID 11356016(2R)-6-Fluoro-3,4-dihydro-2-((2R)-2-oxiranyl)-2H-1-benzopyranYield 100%

Procedure

The resulting catalyst residue was dissolved in (2R)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene (0.97 g), (2R)-6-fluoro-2-[(2R)-oxiran-2-yl]-3,4-dihydro-2H-chromene (0.97 g) [(R,R)-,(R,S)-epoxide diastereoisomeric mixture)] and MTBE (2.36 ml) and the mixture obtained was treated with H2O (0.099 g).

Sources & evidence

ORD record: ord-1d76b385358d4110a70d34014b05bc9f
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003810B2

Reaction notes

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