Tetrahydrofuran → HCID 86588245, compound
Reaction equation
[Li+].CC([N-][CH:6]([CH3:8])[CH3:7])C.[CH2:9]1[CH2:14][CH2:13]CCC1.[C:15]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[CH3:16].ICCC[Si:27]([O:32]C)([O:30][CH3:31])[O:28][CH3:29].[CH2:34]1COCC1>>[C:14]([O:32][Si:27]([O:30][CH3:31])([O:28][CH3:29])[CH2:8][CH2:6][CH2:7][CH2:16][C:15]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:13])([CH3:9])[CH3:34]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a 1.5 M solution of LDA.THF in cyclohexane (200.00 mL, 300.00 mmol) and THF (400 mL), cooled to −78° C. in a dry ice/acetone bath, t-butyl acetate (34.85 g, 300.00 mmol) was added dropwise over 15 min. After 1 h at −78° C., 3-iodopropyltrimethoxysilane (43.53 g, 150.00 mmol) was added dropwise over 15 min. The reaction mixture was allowed to stir at −78° C. for 1 h, sealed with a teflon stopper, and kept in a freezer at −15° C. for 3 days. The cold reaction mixture was vacuum filtered through silica gel (500 mL), eluted with 1:1 hexanes/THF (1000 mL), and concentrated to provide 60.10 g of a pale yellow oil. A quick distillation produced the volatile components, and 27.14 g of a colorless oil was recovered: bp 80-110° C. (0.7-1.0 mm). This material was purified by fractional distillation to provide 14.39 g (30%) of a colorless oil: bp 75-6° C. (0.06 mm); 1H NMR (CDCl3) δ 3.53 (s, OMe), 2.22 (t, CHcCO), 1.63 (quinet, CH2), 1.45 (m, CH2), 1.45 (s, tBuO), 1.31 (s, tBu), 0.62 (m, CH2Si).
Workup
- waitkept in a freezer at −15° C. for 3 days
- customThe cold reaction mixture
- filtrationfiltered through silica gel (500 mL)
- washeluted with 1:1 hexanes/THF (1000 mL)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-47deac4e1bc24976b6a13b621ce9a4ba
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06913865B2
Reaction notes
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