Ethyl bromoacetate → (2,3-Dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-acetic acid ethyl ester

HRID 1825689Notes

Reaction equation

HRID 1825689 reaction equation
[O:1]1[CH:6]([CH2:7][OH:8])[CH2:5][O:4][C:3]2=[CH:9][S:10][CH:11]=[C:2]12.O1CCCC1.[H-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(OCC)(=O)C>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][O:8][CH2:7][CH:6]1[O:1][C:2]2=[CH:11][S:10][CH:9]=[C:3]2[O:4][CH2:5]1)[CH3:25]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 160674382,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

Product 1

HCID 20758020(2,3-Dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(2,3-Dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol (6.9 g, 40 mmol) was dissolved into tetrahydrofuran (100 mL), blanketed by nitrogen. Sodium hydride (1.9 g) was added in portions after which the reaction mixture was stirred for another 30 min. Then ethyl bromoacetate (5.3 mL) was added dropwise and stirring was continued for another hour at 25° C. The reaction mixture was then poured into ethyl acetate, washed with 1M hydrochloric acid, washed with a 1M aqueous solution of sodium hydrogen carbonate and concentrated. This resulted in quantitative formation of pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-ylmethoxy)-acetic acid ethyl ester as demonstrated by NMR and mass spectroscopy.

Workup

  1. stirringstirring
  2. waitwas continued for another hour at 25° C
  3. washwashed with 1M hydrochloric acid
  4. washwashed with a 1M aqueous solution of sodium hydrogen carbonate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-256c500117924787a3bc07947f81e698
Source dataset
uspto-grants-2006_05
Patent number
US07048874B2

Reaction notes

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