Triethylsilane → HCID 118324062, compound

HRID 1778295Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)O)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(Cl)Cl.[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[C:13]3/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of (E)-bis(4-chlorophenyl)(4-styrylquinolin-6-yl)methanol (18 mg, 0.0373 mmol) and triethylsilane (0.0238 mL, 0.149 mmol) in CH2Cl2 (1 mL) at −78° C. was dropwise added titanium chloride (0.0102 mL, 0.0933 mmol). The resulting mixture was warmed to 0° C. for 20 min. To the reaction was slowly added aq. NaHCO3, ice at 0° C. and CH2Cl2. 1N NaOH was added until the aqueous solution was basic. The aqueous layer was extracted with CH2Cl2 twice. The organics were concentrated and purified by silica column chromatography (20-25% EtOAc/hexanes). The product was found to contain ˜7% cis-isomer based on NMR. The resulting mixture was recrystallized from EtOAc/hexanes to remove the Cis isomer.

Workup

customat 0° C.
extractionThe aqueous layer was extracted with CH2Cl2 twice
concentrationThe organics were concentrated
custompurified by silica column chromatography (20-25% EtOAc/hexanes)
customThe resulting mixture was recrystallized from EtOAc/hexanes
customto remove the Cis isomer

Sources & evidence

ORD record: ord-34414884cce740aba5c113361ac578fa
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266835B2

Reaction notes

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