Potassium Carbonate → (S)-2-Methyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-propan-1-ol

HRID 657531Notes

Reaction equation

Br[CH2:2][C@@H:3]([CH3:6])[CH2:4][OH:5].C([O-])([O-])=O.[K+].[K+].[CH3:13][C:14]1([CH3:28])[C:18]([CH3:20])([CH3:19])[O:17][B:16]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[O:15]1>CC#N>[CH3:6][C@H:3]([CH2:2][O:27][C:24]1[CH:23]=[CH:22][C:21]([B:16]2[O:17][C:18]([CH3:20])([CH3:19])[C:14]([CH3:28])([CH3:13])[O:15]2)=[CH:26][CH:25]=1)[CH2:4][OH:5]

Participants

Conditions

Temperature: 72 °C

Procedure

(S)-3-Bromo-2-methylpropan-1-ol (6.2 g, 40 mmol) was dissolved in dry CH3CN (100 mL) and dry, pulverized K2CO3 (10.4 g, 75 mmol) was introduced followed by 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (11.0 g, 50 mmol). The reaction mixture was heated at 72° C. for 20 h, cooled and filtered. The filtrate was evaporated to an oil, which was applied to a column of silica gel. Elution initially with hexanes, gradually increasing polarity to a mixture of hexanes/ethyl acetate (3:2) as eluent, provided the title compound (7.56 g, 64%) as an oil.

Workup

customdry
additionwas introduced
temperaturecooled
filtrationfiltered
customThe filtrate was evaporated to an oil, which
washElution initially with hexanes
temperaturegradually increasing polarity
additionto a mixture of hexanes/ethyl acetate (3:2) as eluent

Sources & evidence

ORD record: ord-9df6beb679bd44e7b8a6f8dddd90d002
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076331B2

Reaction notes

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