Acetic Acid → HCID 86732547, compound

HRID 1749662Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[O:14][C:13]([C:15]([C:17]2[CH:18]=[N:19][C:20]([Cl:24])=[C:21]([Cl:23])[CH:22]=2)=[O:16])=[N:12][N:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].CC(O)=O>O1CCCC1.C(O)C>[Si:1]([O:8][CH2:9][C:10]1[O:14][C:13]([CH:15]([C:17]2[CH:18]=[N:19][C:20]([Cl:24])=[C:21]([Cl:23])[CH:22]=2)[OH:16])=[N:12][N:11]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (5-((tert-butyldimethylsilyloxy)methyl)-1,3,4-oxadiazol-2-yl)(5,6-dichloropyridin-3-yl)methanone (70) (1.75 g, 4.51 mmol) in tetrahydrofuran (8.8 mL) and ethanol (8.8 mL) was added sodium tetrahydroborate (0.085 g, 2.25 mmol) at 0° C. under nitrogen atmosphere. The resulting mixture was stirred at 0° C. for 15 min. AcOH was added to the reaction flask and the mixture was extracted with ethyl acetate (50 mL×2). The resulting organic layer was washed with H2O, brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford 1.79 g of the product (71) as a pale yellow oil (quant.).

Workup

extractionthe mixture was extracted with ethyl acetate (50 mL×2)
washThe resulting organic layer was washed with H2O, brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ab995f924dd54c8faec2a02519e12cc7
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156830B2

Reaction notes

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