Water → 5-Chloro-2-(propane-2-sulfonyl)indan-1-ol

HRID 2358288Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH:6]([S:12](C)(=[O:14])=[O:13])[CH2:5]2.C(N[CH:20]([CH3:22])[CH3:21])(C)C.[Li].CI.O>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH:6]([S:12]([CH:20]([CH3:21])[CH3:22])(=[O:14])=[O:13])[CH2:5]2

Participants

Conditions

Temperature: -70 °C

Procedure

200 mg (0.8 mmol) of 5-chloro-2-methylsulfonylindan-1-ol were dissolved in 5 ml of dry tetrahydrofuran. The solution was cooled to −70° C., and 0.4 ml (0.8 mmol) of lithium diisopropylamine (2 M solution in tetrahydrofuran) was added dropwise under an atmosphere of nitrogen. The reaction solution was stirred at −70° C. for 30 min, and 62.2 μl (1 mmol) of methyl iodide were then added. The reaction mixture was warmed to 0° C., water and then ethyl acetate were added, the organic phase was separated off, dried over magnesium sulfate and filtered and the filtrate was concentrated. Chromatographic purification of the residue (silica gel; heptane/ethyl acetate 1/1) gave 5-chloro-2-(propane-2-sulfonyl)indan-1-ol as a wax-like substance.

Workup

temperatureThe reaction mixture was warmed to 0° C.
customthe organic phase was separated off
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated
customChromatographic purification of the residue (silica gel; heptane/ethyl acetate 1/1)

Sources & evidence

ORD record: ord-b3055d3601874f9691e8421caed30c4b
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763662B2

Reaction notes

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