Water → 2-Methoxy-5-[1-(1,3-dithiolan-2-yl)-1-methylethyl]benzaldehyde

HRID 481543Notes

Reaction equation

[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)([CH:4]1[S:8][CH2:7][CH2:6][S:5]1)[CH3:3].[CH3:17][O:18]C(Cl)Cl.O>ClCl.C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:2]([CH:4]2[S:5][CH2:6][CH2:7][S:8]2)([CH3:1])[CH3:3])=[CH:10][C:11]=1[CH:17]=[O:18]

Participants

Conditions

Temperature: -60 °C

Procedure

To a stirred solution of Compound 80 (0.254 g, 1 mmol) in dry CH2 Cl2 (5 ml) was added a solution of TiCl4 in CH2Cl2 (1M, 3 ml) with cooling (-60° C.). After 3 min., to this was added dichloromethyl methyl ether (0.46 g, 4 mmol) dropwise. The reaction mixture was stirred at same temperature for 1 hr. The mixture was poured into water and stirred at room temperature for 15 min. The organic layer was separated and the aqueous layer was extracted with Et2O (50 ml×2). The combined solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give crude product. The crude product was purified by a column chromatography to give Compound 81 (86 mg) as an oil

Workup

stirringstirred at room temperature for 15 min
customThe organic layer was separated
extractionthe aqueous layer was extracted with Et2O (50 ml×2)
washThe combined solution was washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto give crude product
customThe crude product was purified by a column chromatography

Sources & evidence

ORD record: ord-eae49ffcc197424ab29aa825a399a947
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05789423

Reaction notes

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