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

HRID 431302Notes

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 under an atomosphere of nitrogen, 0.4 ml (0.8 mmol) of lithium diisopropylamine (2 M solution in tetrahydrofuran) was added dropwise. 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 was 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-9511df43a6e248128bb0252aea34a235
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06657086B2

Reaction notes

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