Hydrochloric Acid → [4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]methanol

HRID 2114552ノート

反応式

HRID 2114552 の反応式
[N+:1]([C:4]1[CH:8]=[N:7][N:6]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=1[C:17](OCC)=[O:18])([O-:3])=[O:2].[BH4-].[Na+].[Cl-].[NH4+].Cl>C(OCC)(=O)C.CO>[N+:1]([C:4]1[CH:8]=[N:7][N:6]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[C:5]=1[CH2:17][OH:18])([O-:3])=[O:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 866004844-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazole-3-carboxylic acid, ethyl ester

生成物 1

HCID 68877661[4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]methanol収率 89.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazole-3-carboxylic acid, ethyl ester (10 g, 31.7 mmol) in tetrahydroftiran (200 mL) was added methanol (24 mL) followed by sodium borohydride (9.59 g, 8 eq) in one portion. The resulting mixture was stirred at 0° C. for 20 minutes. The reaction mixture was then added to a mixture of saturated aqueous ammonium chloride solution (600 mL) and ethyl acetate (800 mL) in an ice-bath. A solution of 4 N HCl was added with stirring at 0° C. to adjust the pH of the aqueous layer to about 4. The organic layer was separated and washed with brine (1×500 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound (7.76 g) as a reddish oil. M+=273.

後処理

  1. stirringwith stirring at 0° C.
  2. customThe organic layer was separated
  3. washwashed with brine (1×500 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-fae983a8a1d748e591553959eaea0907
出典データセット
uspto-grants-2008_10
特許番号
US07435731B2

反応ノート

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