Benzyl Bromide → Methanesulfonic acid (R)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester

HRID 2407330Notes

Reaction equation

HRID 2407330 reaction equation
[OH:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([CH2:12][O:13][S:14]([CH3:17])(=[O:16])=[O:15])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:18]([O:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([CH2:12][O:13][S:14]([CH3:17])(=[O:16])=[O:15])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86644727Methanesulfonic acid (R)-5-hydroxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester

Product 1

HCID 86644728Methanesulfonic acid (R)-5-benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl esterYield 1.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methanesulfonic acid (R)-5-hydroxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester (0.6 g, 1.69 mmol), benzyl bromide (0.4 g, 2.30 mmol) and potassium carbonate (1.14 g, 8.30 mmol) in acetone (30 ml) was refluxed under nitrogen atmosphere for 5 h. The crude product was crystallized from 2-propanol to yield 8.8 mg of the pure title compound.

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 5 h
  2. customThe crude product was crystallized from 2-propanol

Sources & evidence

ORD record
ord-b54068a208e64cd8960fdb5ef12ce809
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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