Reaction equation
[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]Participants
Conditions
- Temperature
- 0 °C
Procedure
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).
Workup
- waitno substrate left)
- washAfter dilution with ether (200 ml), the solution was washed with water, saturated ammonium chloride (10 ml), brine
- dry with materialdried over anhydrous magnesium sulfate
- customEvaporation of the solvent under reduced pressure
- customgave a clear oil, 1.690 g (97%) which
- customwithout purification
Sources & evidence
- ORD record
- ord-a98069384f194f889f0a923993f1e4d1
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04272437
Linked notes
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