Water → HCID 59217793, compound

HRID 2246490

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1.[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH:29]=[O:30].O>CCCCCC.O1CCCC1>[Br:25][C:26]1[CH:27]=[C:28]([CH:29]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[OH:30])[CH:31]=[CH:32][C:33]=1[O:34][CH3:35]

Participants

Conditions

Temperature: -78 °C

Procedure

14.8 mL of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 8.0 g 1-bromo-4-triisopropylsilylethynyl-benzene in 80 mL dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 5.1 g 3-bromo-4-methoxy-benzaldehyde dissolved in 20 mL tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm to ambient temperature overnight. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1).

Workup

additionare added dropwise over 15 min
waitThe resulting solution is left in the cooling bath
temperatureto warm to ambient temperature overnight
extractionthe mixture is extracted with ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulfate
customthe solvent is removed
customThe residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1)

Sources & evidence

ORD record: ord-c585e4de99e748a285166be8d639f9b9
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687469B2

Linked notes

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