Lithium hydroxide, monohydrate → 4-(4-(2-Tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoic acid

HRID 453515ノート

反応式

HRID 453515 の反応式
[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)=[C:10]([C:25]#[N:26])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O>O1CCOCC1.Cl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[C:10]([C:25]#[N:26])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 68466372Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate

生成物 1

HCID 684683974-(4-(2-Tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoic acid収率 65.3%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
10 °C

実験手順

Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate (11.60 g, 31.57 mmol) was dissolved in dioxane (160 mL) and the solution was cooled to 10° C. in an ice bath. LiOH—H2O, 1M (37.89 ml, 37.89 mmol) was added to the solution and the mixture was stirred at ambient temperature for 5 hours. The mixture was diluted with 2N HCl (100 mL) and CH2Cl2 (200 mL). Layers were separated and aqueous layer was extracted with CH2Cl2. The combined extracts were washed with brine (100 mL), dried over MgSO4, filtered through a Celite pad and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to provide 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoic acid (7.29 g) as a white solid.

後処理

  1. customLayers were separated
  2. extractionaqueous layer was extracted with CH2Cl2
  3. washThe combined extracts were washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a Celite pad
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-5d38aa6cbc734074b97d78efcdf90125
出典データセット
uspto-grants-2013_07
特許番号
US08492437B2

反応ノート

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