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

HRID 489588

反応式

HRID 489588 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 was removed by filtration and the filtrate was washed with acidic water and aqueous, saturated NaCl. Subsequently, the solvent was 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 was removed by filtration
  3. washthe filtrate was washed with acidic water
  4. customSubsequently, the solvent was 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-4e91a7b2b6004e24aa5027f1d3b8ca0c
出典データセット
uspto-grants-2005_12
特許番号
US06977390B2

関連ノート

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