Potassium Hydroxide → (S)-(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

HRID 38994

Reaction equation

HRID 38994 reaction equation
C([O:3][C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][C@H:13]1[CH2:15][O:14]1)=O.[OH-].[K+]>O1CCOCC1>[Br:10][C:8]1[CH:7]=[CH:6][C:5]2[O:11][CH2:12][C@H:13]([CH2:15][OH:14])[O:3][C:4]=2[CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 541488055-Bromo-2-[(2R)-oxiran-2-ylmethoxy]phenyl formate

Product 1

HCID 23394142(S)-(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Preparation according to Preparation 8 using 5-bromo-2-[(2R)-oxiran-2-ylmethoxy]phenyl formate (7.0 g, 25 mmol), dioxane (30 ml) and KOH (10%, 15 ml), stirred for 1 h. Purification on flash column chromatography (Isooctane/EtOAc). Crude yield: 3.7 g. MS m/z (rel. intensity, 70 eV) 245 (M+, 97) 244 (M+, bp), 189 (48), 188 (50) 79 (39).

Workup

  1. customPreparation
  2. customPurification on flash column chromatography (Isooctane/EtOAc)

Sources & evidence

ORD record
ord-e8b8ba4163e34860aa156c4fc4e5c70d
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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