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

HRID 23753

반응식

HRID 23753 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-ffcbd940d19447389ed82df3bbd1fbd1
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852830B2

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