Sodium Hydroxide → (2R)-6-Fluoro-3,4-dihydro-2-((2R)-2-oxiranyl)-2H-1-benzopyran

HRID 661584Notes

Reaction equation

Cl[CH2:2][C@H:3]([C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)[OH:4].[OH-].[Na+]>CC(O)C.C1(C)C=CC=CC=1.O>[F:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[O:6][C@@H:5]([C@H:3]1[CH2:2][O:4]1)[CH2:14][CH2:13]2

Participants

Conditions

Temperature: 0 °C

Procedure

The compound (S*)-2-chloro-1-((R*)-6-fluoro-3,4-dihydro-2H-chromen-2-yl)-ethanol obtained in Example 1 (320 mg, 1.387 mmoles) is dissolved in i-PrOH (2 ml) under nitrogen and the reaction mixture is cooled to 0° C. On the magnetically stirred mixture is added a 2M aqueous solution of sodium hydroxide (1.39 ml) in 10 min. The mixture is stirred for 2 hours at 0° C., then diluted with toluene (5 ml) and transferred in a separator funnel. The biphasic mixture is further diluted with toluene (5 ml) and demi water (5 ml) and the phases are separated. The organic phase is washed with demi water (10 ml) and concentrated under vacuum to yield (R*)-6-fluoro-3,4-dihydro((R*)-oxiran-2-yl)-2H-chromen as yellow oil (200 mg, 74%, 98% de via GC).

Workup

customtransferred in a separator funnel
customthe phases are separated
washThe organic phase is washed with demi water (10 ml)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-d94b549d539d415e856d6a78400dcaac
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084629B2

Reaction notes

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