tert-Butanol → 4-Pentynoic acid, 1,1-dimethylethyl ester

HRID 1482250

反応式

HRID 1482250 の反応式
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].[CH3:8][C:9](O)([CH3:11])[CH3:10].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([O:7][C:9]([CH3:11])([CH3:10])[CH3:8])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5]

参加物

6

反応物 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 224644-Pentynoic acid

生成物 1

HCID 108773414-Pentynoic acid, 1,1-dimethylethyl ester収率 91%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Pent-4-ynoic acid (5.0 g, 51.0 mmol), 2-methylpropan-2-ol (7.56 g, 102.0 mmol) and 4-(dimethylamino)pyridine (0.31 g, 2.54 mmol) were dissolved in DCM (17.5 ml), a solution of dicyclohexylcarbodiimide (11.6 g, 56.2 mmol) in DCM (17.5 ml) was added and the mixture was stirred at room temperature overnight. The white solid in the reaction solution was removed by filtration, after which the filtrate was washed with a 0.5 M aqueous hydrochloric acid solution and a saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. The residue obtained by filtration and concentration under reduced pressure was purified by silica gel column chromatography (DCM) to afford the title compound (Compound SP429) (7.15 g, 91.0%).

後処理

  1. customThe white solid in the reaction solution was removed by filtration
  2. washafter which the filtrate was washed with a 0.5 M aqueous hydrochloric acid solution
  3. dry with materiala saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate
  4. customThe residue obtained by filtration and concentration under reduced pressure
  5. customwas purified by silica gel column chromatography (DCM)

出典と根拠

ORDレコード
ord-5af35e94f05a440e8c6be544e402046b
出典データセット
uspto-grants-2016_08
特許番号
US09409952B2

関連ノート

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