Cyclohexane → HCID 85832944, compound
Reaction equation
[Li+].CC([N-]C(C)C)C.C1CCCCC1.[C:15]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[CH3:16].I[CH2:24][CH2:25][CH2:26][Si:27]([O:32][CH3:33])([O:30][CH3:31])[O:28][CH3:29]>C1COCC1>[CH3:29][O:28][Si:27]([O:32][CH3:33])([O:30][CH3:31])[CH2:26][CH2:25][CH2:24][CH2:16][C:15]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]Participants
Conditions
- Temperature
- -78 °C
Procedure
To an 1.5 M solution of LDA.THF in cyclohexane (53.33 mL, 80.00 mmol) and THF (160 mL), cooled to −78° C. in a dry ice/acetone bath, t-butyl acetate (9.29 g, 80.00 mmol) was added dropwise over 15 min. After 1 h at −78° C., 3-iodopropyltrimethoxysilane (23.21 g, 80.00 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 (300 mL), eluted with 1:1 hexanes/THF (600 mL), and concentrated to provide 21.48 g of a pale yellow oil. A quick distillation produced the volatile components, and 17.76 g of a colorless oil was recovered: bp 55-85° C. (0.2 mm). This material was purified by fractional distillation to provide 6.26 g (28%) of a colorless oil: bp 62-3° C. (0.03 mm); 1 HNMR (CDCl3) δ 3.56 (s, OMe), 2.21 (t, CH2CO), 1.62 (quintet, CH2), 1.45 (m, CH2), 1.44 (s, tBu), 0.66 (m, CH2Si).
Workup
- waitkept in a freezer at −15° C. for 3 days
- customThe cold reaction mixture
- filtrationfiltered through silica gel (300 mL)
- washeluted with 1:1 hexanes/THF (600 mL)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cbb18431a2294765a87bf018f71a66db
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06913865B2
Reaction notes
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