Water → (1R)-1-[(2S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]ethane-1,2-diol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@H:7]([C@H:12]1[CH2:16][O:15]C(C)(C)[O:13]1)[CH2:6][CH2:5]2.O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@H:7]([C@H:12]([OH:13])[CH2:16][OH:15])[CH2:6][CH2:5]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
(S)-6-fluoro-3,4-dihydro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene (1.10 g, 4.4 mmol) was dissolved in acetic acid (9 ml) and demi water (3 ml). The reaction mixture was stirred vigorously and heated to 65° C. After 2.5 h at 60° C. the reaction mixture was cooled to 25° C. The solution was then concentrated in vacuo to obtain a vetrous oil. Chromatographic separation on silica of the crude, using a mixture of heptane:ethyl acetate 1:1 as eluent, furnished 0.40 g of (R)-1-((S)-6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethane-1,2-diol as a white solid (43% yield).
Workup
- temperatureAfter 2.5 h at 60° C. the reaction mixture was cooled to 25° C
- concentrationThe solution was then concentrated in vacuo
- customto obtain a vetrous oil
- customChromatographic separation on silica of the crude
- additiona mixture of heptane:ethyl acetate 1:1 as eluent
Sources & evidence
- ORD record
- ord-4c3765e3731344ca8a5b04bb2c92e480
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258323B2
Reaction notes
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