Benzene → 2,3-O-Isopropylidene-L-gulonolactone, 2,3-O-Isopropylidene-L-gulono-1,4-lactone, 2,3-O-(1-Methylethylidene)-L-gulonic Acid |A-Lactone, 94840-08-1

HRID 1723485

反応式

HRID 1723485 の反応式
CC1(C)[O:6][CH:5]([CH:7]2[O:12][C:10](=[O:11])[CH:9]3[O:13][C:14]([CH3:17])([CH3:16])[O:15][CH:8]23)[CH2:4][O:3]1.C(OCC)(=O)C.CCCCCC.C1C=CC=CC=1.C(OCC)(=O)C.CC(C)=O>C(O)(=O)C.O>[CH3:16][C:14]1([CH3:17])[O:13][CH:9]2[C:10]([O:12][CH:7]([CH:5]([OH:6])[CH2:4][OH:3])[CH:8]2[O:15]1)=[O:11]

参加物

6

反応物 4

HCID 241BenzeneHCID 5682882,3:5,6-Di-O-isopropylidene-L-gulonolactoneHCID 21226206Ethyl acetate hexaneHCID 21584569Ethylacetate acetone

生成物 1

HCID 141064282,3-O-Isopropylidene-L-gulonolactone, 2,3-O-Isopropylidene-L-gulono-1,4-lactone, 2,3-O-(1-Methylethylidene)-L-gulonic Acid |A-Lactone, 94840-08-1収率 79%

試薬・触媒・溶媒 1

HCID 21899381Acetic acid--water (1/1)溶媒

反応条件

温度
30 °C

実験手順

2,3:5,6-Di-O-isopropylidene-L-gulonolactone (22.89 g, 88.7 mmol) was dissolved in acetic acid/water (7:1, 200 ml) and stirred at 30° C. for 16 h when t.l.c. (ethyl acetate/hexane 1:1) revealed no starting material (Rf 0.5) and one major product (Rf 0.1). The solvent was removed under reduced pressure to give a yellow oil. Trituration with benzene (50 ml) gave a solid which was shaken with ethyl acetate/acetone (1:1, 250 ml). The resulting suspension was filtered and solvents removed under reduced pressure to yield an amorphous yellow solid, which was recrystallized from ethyl acetate to yield 2,3-O-isopropylidene-L-gulonolactone, (14.31 g, 79%) as a white crystalline solid, m.p. 139°-141° C., [α]D20 +76.2° (C, 1 in acetone).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customto give a yellow oil
  3. filtrationThe resulting suspension was filtered
  4. customsolvents removed under reduced pressure
  5. customto yield an amorphous yellow solid, which
  6. customwas recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-0c084429bd6843f69c8cd616e1d823cc
出典データセット
uspto-grants-1989_08
特許番号
US04861892

関連ノート

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