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

HRID 1680337

반응식

HRID 1680337 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a98069384f194f889f0a923993f1e4d1
출처 데이터셋
uspto-grants-1981_06
특허 번호
US04272437

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