Potassium Hydroxide → [(2S)-7-(Trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

HRID 39013Notes

Reaction equation

HRID 39013 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([S:11]([C:14]([F:17])([F:16])[F:15])(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=1[O:18][CH2:19][C@H:20]1[CH2:22][O:21]1)(=O)C.[OH-].[K+]>O1CCOCC1>[F:16][C:14]([F:15])([F:17])[S:11]([C:9]1[CH:8]=[CH:7][C:6]2[O:18][CH2:19][C@H:20]([CH2:22][OH:21])[O:4][C:5]=2[CH:10]=1)(=[O:12])=[O:13]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 866529492-[(2R)-Oxiran-2-ylmethoxy]-5-[(trifluoromethyl)sulfonyl]phenyl acetate

Product 1

HCID 67198869[(2S)-7-(Trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Preparation according to Preparation 20 using 2-[(2R)-oxiran-2-ylmethoxy]-5-[(trifluoromethyl)sulfonyl]phenyl acetate (1.0 g, 3.7 mmol), dioxane (10 ml) and KOH (10%, 10 ml), the mixture stirred at RT for 1 h. Yield 1.0 g. MS m/z (rel. intensity, 70 eV) 298 (M+, 29), 229 (72), 165 (bp), 107 (67), 79 (33).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-1acb426b52e149b98ebdc866b3fc5ae3
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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