Hydrochloric Acid → HCID 57999457, compound

HRID 511990Notes

Reaction equation

[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([C:11]([CH3:19])([CH3:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]=[C:7]([O:20][CH2:21][O:22][CH3:23])[CH:6]=1.[Li]CCCC.[B:29](OC)([O:32]C)[O:30]C.Cl>C1COCC1.O>[CH3:23][O:22][CH2:21][O:20][C:7]1[CH:8]=[C:9]([C:11]([CH3:18])([CH3:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:10]=[C:5]([O:4][CH2:3][O:2][CH3:1])[C:6]=1[B:29]([OH:32])[OH:30]

Participants

Conditions

Temperature: -10 °C

Procedure

1,3-Bis(methoxymethoxy)-5-(1,1-dimethylheptyl)-benzene (50) (1 equiv.) was dissolved in dry THF (10 mL). The solution was cooled to −10° C. and n-BuLi (1.1 equiv. using 1.6 solution in hexanes) was added dropwise. The mixture was stirred for an additional 1.5 h, then it was cooled to −78° C. and (MeO)3B (5 equiv.) was added. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was diluted with water, stirred for 30 min and the pH was adjusted to 4 with dilute aqueous HCl. The mixture was extracted with EtOAc, the organic layer was dried (MgSO4) and the solvent was evaporated. Purification by flash column chromatography (hexane-acetone) gave the title compound in 81% yield.

Workup

temperatureit was cooled to −78° C.
temperatureto warm to room temperature
stirringstirred overnight
stirringstirred for 30 min
extractionThe mixture was extracted with EtOAc
dry with materialthe organic layer was dried (MgSO4)
customthe solvent was evaporated
customPurification by flash column chromatography (hexane-acetone)

Sources & evidence

ORD record: ord-225e7d07db9942889bdcefa1f34a6eeb
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102622B2

Reaction notes

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