Water → (2S)-2-[(1,1-Dimethylethoxy)methyl]oxirane
Reaction equation
[CH2:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH:2]1[O:4][CH2:3]1.O>CC(C1C=C(C(C)(C)C)C(=O)/C(=C/N[C@H]2[C@H](N/C=C3/C=C(C(C)(C)C)C=C(C(C)(C)C)C/3=O)CCCC2)/C=1)(C)C.[Co].C(O)(=O)C.O1CCCC1>[CH2:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[C@H:2]1[O:4][CH2:3]1Participants
Conditions
- Temperature
- 0 °C
Procedure
In a 500 ml round bottomed flask equipped with thermometer and a magnetic stirrer and an ice bath 6.04 g (1R,2R)-(−)-1,2-cyclohexanediamino-N,N′-bis-(3,5-di-t-butylsalicylidene) cobalt (II) (10 mmol; Strem Chemicals) and 260.38 g rac tert-butyl glycidyl ether (2000 mmol) and 2.40 g acetic acid (40 mmol) and 20 ml THF (tetrahydrofurane) were cooled under stirring to 0° C. and 19.82 g deionized water (1100 mmol) were added all at once. The dark red reaction mixture was stirred under an air atmosphere for 0.5 h at 0° C. and for 23 h at RT. Vacuum distillation over a column filled with “Fenske” glass rings (20×2 cm column; “Fenske” glass rings Ø≅4 mm) afforded 113.2 g (43.5%) (S)-tert-butyl glycidyl ether (S)-1 as colorless liquid, b.p. 84-86° C./100 mbar.
Workup
- temperaturewere cooled
- customThe dark red reaction mixture
- stirringwas stirred under an air atmosphere for 0.5 h at 0° C. and for 23 h at RT
- distillationVacuum distillation over a column
- additionfilled with “Fenske” glass rings (20×2 cm column; “Fenske” glass rings Ø≅4 mm)
Sources & evidence
- ORD record
- ord-cc82c70d62a34419b30fd9610fd1277d
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07956201B2
Reaction notes
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