2-Naphthalenecarboxaldehyde → HCID 59749557, compound

HRID 1174690Notes

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].[Li]CCCC.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[CH:35]=[O:36]>C1COCC1>[CH3:1][N:2]([CH3:11])[S:3]([N:6]1[CH:10]=[C:9]([CH:35]([OH:36])[C:26]2[CH:27]=[CH:28][C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:25]=2)[N:8]=[C:7]1[Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])(=[O:4])=[O:5]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of N,N-dimethyl imidazole-1-sulfonamide (commercially available from Aldrich) (2.0 g, 11.4 mmol) in THF (50 mL) at −78° C. was treated with nBuLi (4.6 mL of a 2.5 M soln) for 1 h. Solid tert-butyl-dimethylsilanyl chloride (TBSCl) (1.72 g, 11.4 mmol) in THF (10 mL) was added at rt for 16 h. The mixture was cooled to −20° C. and treated with nBuLi (4.6 mL of a 2.5 M soln) for 1 h. 2-Naphthaldehyde (1.78 g, 11.4 mmol) in THF (10 mL) was added and the mixture was stirred for 3 h at rt. The mixture was washed with brine and dried over Na2SO4. The solvent was removed under vacuum and the residue was purified by chromatography on silical gel with 25% EtOAc:hexane to give 2-(tert-butyl-dimethyl-silanyl)-4-(hydroxy-naphthalen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (Intermediate-I1) 2.6 g (50%).

Workup

washThe mixture was washed with brine
dry with materialdried over Na2SO4
customThe solvent was removed under vacuum
customthe residue was purified by chromatography on silical gel with 25% EtOAc

Sources & evidence

ORD record: ord-da40f3663f334b78a8020db8a24b6e70
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838545B2

Reaction notes

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