Water → HCID 73853769, compound

HRID 1243832Notes

Reaction equation

HRID 1243832 reaction equation
[CH:1]1([C:4]([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:11][C:10]=3[N:9]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[N:8]=2)=[N:5][OH:6])[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:39][CH2:40][O:41][CH3:42].O>O1CCCC1>[CH3:42][O:41][CH2:40][CH2:39][O:6][N:5]=[C:4]([CH:1]1[CH2:2][CH2:3]1)[C:7]1[C:15]2[CH:14]=[CH:13][C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:11][C:10]=2[N:9]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 136358385HCID 136358385, compound

Product 1

HCID 73853769HCID 73853769, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 0.35 g of the E isomer of cyclopropyl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone oxime in 10 cm3 of tetrahydrofuran is added dropwise to a suspension of 0.036 g of sodium hydride (at 60% in oil) in 7 cm3 of tetrahydrofuran. After stirring the reaction mixture for about 2 hours in the region of 20° C., a solution of 0.16 g of 1-bromo-2-methoxyethane in 5 cm3 of tetrahydrofuran is poured into the solution obtained. After stirring in the region of 20° C. for about two and a half hours, 5 cm3 of water are added and the solution is concentrated to dryness under reduced pressure (13 kPa). The residue is taken up in 20 cm3 of water and extracted with three times 40 cm3 of dichloromethane. The organic phases are combined, dried over magnesium sulphate, filtered and concentrated. After flash chromatography on a column of silica [eluent: dichloromethane/ethyl acetate (99/1 by volume)], 0.32 g of the E isomer of cyclopropyl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone O-(2-methoxyethyl)oxime is thus obtained in the form of a resin, the characteristics of which are as follows:

Workup

  1. customobtained
  2. stirringAfter stirring in the region of 20° C. for about two and a half hours
  3. concentrationthe solution is concentrated to dryness under reduced pressure (13 kPa)
  4. extractionextracted with three times 40 cm3 of dichloromethane
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-af1cef23f6ce42bcb8584004ff1911e6
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

Loading…