Ethyl Acetate → 2,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

HRID 23752

反応式

HRID 23752 の反応式
[OH:1][CH2:2][CH:3]1[O:8][C:7]2=[C:9](C(O)=O)[S:10][C:11](C(O)=O)=[C:6]2[O:5][CH2:4]1.C(OCC)(=O)C>CN(C)C(=O)C.N1C2C(=CC=CC=2)C=CC=1>[O:8]1[CH:3]([CH2:2][OH:1])[CH2:4][O:5][C:6]2=[CH:11][S:10][CH:9]=[C:7]12

参加物

5

反応物 2

HCID 8857Ethyl AcetateHCID 219583572-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid

生成物 1

HCID 160674382,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

試薬・触媒・溶媒 2

HCID 7047Quinoline触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

2-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid (48 g, 0.184 mol) was dissolved in N,N-dimethylacetamide (500 mL), and Cu2Cr2O7 (8.6 g) and quinoline (15 drops) were added. This mixture was subsequently stirred for 2 hours at 150° C., after which it was cooled to 25° C. It was then poured into ethyl acetate, the catalyst removed by filtration and the filtrate washed with acidic water and a saturated aqueous solution of sodium chloride. The solvent was then removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol was isolated by vacuum distillation (115-120° C.; 0.05 mm Hg).

後処理

  1. temperatureafter which it was cooled to 25° C
  2. customthe catalyst removed by filtration
  3. washthe filtrate washed with acidic water
  4. customThe solvent was then removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol
  5. customwas isolated by vacuum distillation (115-120° C.; 0.05 mm Hg)

出典と根拠

ORDレコード
ord-34bd2a2f4aff47e78ac53ebf4e1f16b8
出典データセット
uspto-grants-2005_02
特許番号
US06852830B2

関連ノート

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