Diisobutylaluminum hydride → 2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethanol

HRID 528489Notes

Reaction equation

C[O:2][C:3](=O)[CH:4]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH:5]1[CH2:7][CH2:6]1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[C:12]([Si:9]([CH3:11])([CH3:10])[O:8][CH:4]([CH:5]1[CH2:7][CH2:6]1)[CH2:3][OH:2])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (tert-butyl-dimethyl-silanyloxy)-cyclopropyl-acetic acid methyl ester (1.66 g, 6.79 mmol) in DCM (27 mL) at −78° C. under a nitrogen atmosphere was added DIBAL-H (20.37 mL, 20.37 mmol, 1.0M in toluene) dropwise. The reaction mixture was stirred at −78° C. for 2.5 hours then at 0° C. for 1 hour before being quenched with Rochelle's salt (30 mL, 1M aqueous solution). The mixture was extracted with ethyl acetate (3×30 mL) before the combined organic phases were dried (Na2SO4) and concentrated in vacuo giving 2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethanol as a pale orange oil (764 mg, 52%). 1H NMR (400 MHz, CDCl3): δ 3.66-3.49 (2H, m), 3.09 (1H, ddd, J=7.96, 6.40, 3.80 Hz), 1.96 (1H, dd, J=7.43, 5.46 Hz), 0.91 (9H, s), 0.91-0.82 (1H, m), 0.57-0.43 (2H, m), 0.34-0.24 (1H, m), 0.23-0.14 (1H, m), 0.11 (3H, s), 0.07 (3H, s).

Workup

customat 0° C. for 1 hour before being quenched with Rochelle's salt (30 mL, 1M aqueous solution)
extractionThe mixture was extracted with ethyl acetate (3×30 mL) before the combined organic phases
dry with materialwere dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-27e74c02dc6f4c15b9ce76da8e9d6eb3
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346817B2

Reaction notes

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