Triethylamine → (1R,2R)-ethyl 2-((methylsulfonyloxy)methyl)cyclopropanecarboxylate

HRID 355239

反応式

HRID 355239 の反応式
[OH:1][CH2:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7].[S:11](Cl)([CH3:14])(=[O:13])=[O:12].C(N(CC)CC)C>O1CCCC1>[CH3:14][S:11]([O:1][CH2:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:13])=[O:12]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 29920784Ethyl (1R,2R)-2-(hydroxymethyl)cyclopropanecarboxylate

生成物 1

HCID 53825740(1R,2R)-ethyl 2-((methylsulfonyloxy)methyl)cyclopropanecarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of trans-ethyl 2-hydroxymethyl-1-cyclopropanecarboxylate (1.136 g, 7.88 mmol) in dry tetrahydrofuran (20 ml) was cooled to 0° C. (ice bath), treated dropwise with mesyl chloride (0.675 ml, 8.66 mmol) and then treated immediately with triethylamine (1.32 ml, 9.52 mmol). This solution was stirred at 0° C. for 1.5 h (tlc indicated no substrate left). After dilution with ether (200 ml), the solution was washed with water, saturated ammonium chloride (10 ml), brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure gave a clear oil, 1.690 g (97%) which was used as such for the next step without purification. ir (film) νmax : 1720 cm-1 (C=O); 1Hmr (CDCl3) δ: 4.13 (2H, q, J=7, CH2 --CH3, 3.05 (2H, s, CH2 --OMs), 2.0~0.6 (4H, m, cyclopropyl), 1.27 ppm (3H, t, J=7, CH3 --CH2).

後処理

  1. waitno substrate left)
  2. washAfter dilution with ether (200 ml), the solution was washed with water, saturated ammonium chloride (10 ml), brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent under reduced pressure
  5. customgave a clear oil, 1.690 g (97%) which
  6. customwithout purification

出典と根拠

ORDレコード
ord-41c9eeaee4d84aefa6df148d6cab7119
出典データセット
uspto-grants-1983_03
特許番号
US04378314

関連ノート

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