Benzoyl chloride → D-Ribitol, 1,4-dideoxy-1,4-epithio-2,3-O-(1-methylethylidene)-, 5-benzoate

HRID 1268719ノート

反応式

HRID 1268719 の反応式
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]2[CH2:7][S:8][C@H:9]([CH:10]=[O:11])[C@H:4]2[O:3]1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]2[CH2:7][S:8][C@H:9]([CH2:10][O:11][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C@H:4]2[O:3]1

参加物

4

反応物 2

HCID 7412Benzoyl chlorideHCID 86601630HCID 86601630、化合物

生成物 1

HCID 10859362D-Ribitol, 1,4-dideoxy-1,4-epithio-2,3-O-(1-methylethylidene)-, 5-benzoate収率 99%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a solution of 111 (2.1 g, 11.1 mmol) in pyridine (20 mL) was added benzoyl chloride (1.9 g, 13.4 mmol) at 0° C. and the reaction mixture was stirred for 6 h at room temperature before being quenched with methanol. The reaction mixture was evaporated under reduced pressure. The residue was then taken up in diethyl ether (50 mL), and the pyridinium salt was filtered and washed with diethyl ether. The combined organic layer was concentrated and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1) to afford the benzoate 112 (3.2 g, 99%) as a colorless oil: 1H NMR (CDCl3) δ 1.26 (s, 3H, CH3), 1.47 (s, 3H, CH3), 2.87 (dd, 1H, J=13.2, 1.5 Hz, 6-CHH), 3.11 (dd, 1H, J=13.2, 4.9 Hz, 6–CHH), 3.57 (m, 1H, 4-H), 4.25 (dd, 1H, J=11.5, 8.0 Hz, BzOCHH), 4.35 (dd, 1H, J=11.4, 5.8 Hz, BzOCHH), 4.72 (dd, 1H, J=5.6, 1.2 Hz, 6a-H), 4.91 (td, 1H, J=4.4, 1.2 Hz, 3a-H), 7.35–7.99 (m, 5H, Ph); FAB-MS m/z 294 (M+); Anal. Calcd for C15H18O4S: C, 61.20; H, 6.16; S, 10.89. Found: C, 60.99; H, 6.42; S, 10.77.

後処理

  1. custombefore being quenched with methanol
  2. customThe reaction mixture was evaporated under reduced pressure
  3. filtrationthe pyridinium salt was filtered
  4. washwashed with diethyl ether
  5. concentrationThe combined organic layer was concentrated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-67efb869a3ac478a986ff4df461b4370
出典データセット
uspto-grants-2007_04
特許番号
US07199127B2

反応ノート

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