Hexane → HCID 69832482, compound

HRID 1935754Notes

Reaction equation

HRID 1935754 reaction equation
[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)(=[O:5])=[O:4].C([Li])CCC.CCCCCC.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].[C:31]1([CH:37]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:39](=[O:46])[CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[C:10]([C:39]2([OH:46])[C:40]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:37]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:38]2)=[CH:9][N:8]=[C:7]1[Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])(=[O:4])=[O:5]

Participants

7

Reactant 5

HCID 8058Hexane2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 981461-Indanone, 3-phenyl-HCID 395751N,N-Dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium2×

Product 1

HCID 69832482HCID 69832482, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of imidazole-1-sulfonic acid dimethylamide (1.96 g, 0.0112 mol, prepared according to D. J. Chadwick and R. I. Ngochindo J. Chem. Soc. Perkin Trans. I (1984) 481) in dry tetrahydrofuran (90 ml) under nitrogen was cooled to −78° C. and treated dropwise with 15% n-butyllithium in hexane (8.2 ml, 0.01393 mol). After 30 minutes tert-butyldimethylsilyl chloride (2.1 g, 0.01393 mol) in dry tetrahydrofuran (5 ml) was added and the mixture was allowed to warm to room temperature. After 1.5 hr the mixture was again cooled to −78° C. and treated with 15 % n-butyllithium in hexane (8.5 ml, 0.01360 mol). After 30 minutes 3-phenyl-1-indanone (3.40 g, 0.01633 mol) in dry tetrahydrofuran was added and the mixture was allowed to warm to room temperature during the night. The mixture was quenched with saturated sodium carbonate solution and the solvent was removed under reduced pressure. The residue was dissolved in dichloromethane and washed twice with water, dried, filtered and concentrated under reduced pressure. Purification was done by flash chromatography (elution with a heptane—ethyl acetate gradient).

Workup

  1. temperatureAfter 1.5 hr the mixture was again cooled to −78° C.
  2. temperatureto warm to room temperature during the night
  3. customThe mixture was quenched with saturated sodium carbonate solution
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed twice with water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification
  11. washelution with a heptane—ethyl acetate gradient)

Sources & evidence

ORD record
ord-b322a05f7e9940e9a1d659c163728a1b
Source dataset
uspto-grants-2002_05
Patent number
US06388090B2

Reaction notes

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