Hydrochloric Acid → (4-{[(3S)-3,7-Dimethyloct-6-en-1-yl]oxy}phenyl)boronic acid

HRID 2307205Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C@@H:11]([CH3:18])[CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:4][CH:3]=1.[B:19](OC)([O:22]C)[O:20]C.Cl>O1CCCC1>[CH3:18][C@@H:11]([CH2:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH2:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([B:19]([OH:22])[OH:20])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2.5 M n-Butylithium in hexanes (49.3 cm3, 0.12 mol) was added dropwise to a cooled (−78° C.) solution of 1-bromo-4-[(S)-3,7-dimethyloct-6-enyloxy]benzene (35 g, 0.11 mol) in tetrahydrofuran (350 cm3). The resultant solution was stirred at this temperature for 1 h and then trimethyl borate (23.8 g, 0.23 mol) was added dropwise to the mixture while maintaining the temperature at −78° C. 20% hydrochloric acid (250 cm3) was added and the resultant mixture was stirred for 1h and then extracted into diethyl ether (2×200 cm3). The combined organic layers were washed with water (2×100 cm3) and dried (MgSO4). After filtration the solvent was removed under reduce pressure to yield 20.35 g (65%) of the desired product.

Workup

extractionextracted into diethyl ether (2×200 cm3)
washThe combined organic layers were washed with water (2×100 cm3)
dry with materialdried (MgSO4)
filtrationAfter filtration the solvent
customwas removed

Sources & evidence

ORD record: ord-c296808afadb466db9a93dea22675a6d
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06830831B2

Reaction notes

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