Water → HCID 66971319, compound

HRID 1365027Notes

Reaction equation

HRID 1365027 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([CH:14]=[O:15])=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:11]([CH:24]([CH3:26])[CH3:25])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([Mg]Br)=[CH:31][CH:30]=1.O>O1CCCC1>[CH2:1]([O:8][C:9]1[C:13]([CH:14]([C:32]2[CH:33]=[CH:34][C:29]([O:28][CH3:27])=[CH:30][CH:31]=2)[OH:15])=[C:12]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[N:11]([CH:24]([CH3:26])[CH3:25])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23079533HCID 23079533, compoundHCID 178491912HCID 178491912, compound

Product 1

HCID 66971319HCID 66971319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-benzyloxy-4-formyl-1-isopropyl-5-(4-methoxyphenyl)-1H-pyrazole (0.14 g) in tetrahydrofuran (1.8 mL) was added a solution of 4-methoxyphenylmagnesium bromide in tetrahydrofuran (0.5 mol/L, 0.96 mL) at room temperature and the mixture was stirred at room temperature for 1 hour. A small amount of water was added to the reaction mixture and the mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). Further purification by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1-2/1) gave the title compound (0.11 g).

Workup

  1. customthe mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
  2. customFurther purification by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1-2/1)

Sources & evidence

ORD record
ord-1d863c4e1f444cdeb036d9bf63622b2a
Source dataset
uspto-grants-2011_02
Patent number
US07888487B2

Reaction notes

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