Lithiumtriethylborohydride → HCID 77561273, compound

HRID 1797427Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:25])([CH3:24])[O:6][C@H:7]1[CH2:11][C:10](=[O:12])[C:9](=[CH2:13])[C@@H:8]1[CH2:14][Si:15]([CH3:23])([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:4])[CH3:3].C([BH-](CC)CC)C.[Li+]>C1COCC1>[CH3:4][C:2]([Si:5]([CH3:25])([CH3:24])[O:6][CH:7]1[CH2:11][CH:10]([OH:12])[C:9](=[CH2:13])[CH:8]1[CH2:14][Si:15]([CH3:23])([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:1])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.), stirred solution of 36 (4.8 g, 12.81 mmol) in THF (25 mL) in a 100-mL round bottomed flask equipped with an argon inlet was added lithium triethylborohydride (super hydride®, 24.4 mL, 24.4 mmol, 1.0 M THF solution) over a period of 15 minutes. The reaction mixture was stirred at the same temperature for 1 hour and slowly warmed to room temperature to complete the reaction. The reaction mixture was quenched with sodium hydroxide solution (10%, 25 mL) and extracted with ethyl acetate (2×25 mL). The organic layer was separated, washed with brine (50 mL), and dried over magnesium sulfate. Concentration of the organic layer in vacuo gave the crude title compound, 4.58 g in 95% yield in a 8:1 diastereomeric ratio. The title compound was purified by using silica gel flash chromatography ethyl acetate/hexanes (1:4 v/v) to afford the desired diastereomer, 4 g in 83% yield.

Workup

customequipped with an argon inlet
temperatureslowly warmed to room temperature
customthe reaction
customThe reaction mixture was quenched with sodium hydroxide solution (10%, 25 mL)
extractionextracted with ethyl acetate (2×25 mL)
customThe organic layer was separated
washwashed with brine (50 mL)
dry with materialdried over magnesium sulfate

Sources & evidence

ORD record: ord-f223cbc0ae224e85b180b1f11d59fc7e
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034152B2

Reaction notes

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