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Sodium Hydroxide → 2-Methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid

HRID 1802366
ノート
印刷プレビュー

反応式

HRID 1802366 の反応式
C([O:3][C:4](=[O:18])[C:5]([CH3:17])([S:7]([CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)(=[O:9])=[O:8])[CH3:6])C.[OH-].[Na+].CC(OC)(C)C>C1COCC1>[CH3:17][C:5]([S:7]([CH2:10][CH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)(=[O:9])=[O:8])([CH3:6])[C:4]([OH:18])=[O:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 597039342-Methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid ethyl ester

生成物 1

HCID 597039922-Methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid収率 91.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 123 g (0.44 mol) of 2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid ethyl ester in THF (450 mL) are added 663 mL of 2M aqueous sodium hydroxide solution (1.33 mol). The reaction is stirred at room temperature for 1 h. To the reaction mixture is added TBME (1.25 L) and the layers are separated. The aqueous layer is cooled in an ice bath and then acidified with 37% aqueous HCl solution (123 mL). The resulting precipitate is isolated by filtration, washed with water (200 mL) and dried under reduced pressure at 50° C. to afford 101 g of 2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionic acid as white crystalline solids. Yield: 91%; ES-MS: m/z 251 [M+H]; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31-1.45 (2 H, m), 1.49 (6 H, s), 1.70-1.79 (2 H, m), 2.13-2.28 (1 H, m), 3.24 (2 H, d, J=6.60 Hz), 3.28-3.38 (2 H, m), 3.76-3.85 (2 H, m), 13.65 (1 H, br. s.)

後処理

  1. customthe layers are separated
  2. temperatureThe aqueous layer is cooled in an ice bath
  3. customThe resulting precipitate is isolated by filtration
  4. washwashed with water (200 mL)
  5. customdried under reduced pressure at 50° C.

出典と根拠

ORDレコード
ord-acebf2455d6747789e03a0a576ded831
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08349871B2

反応ノート

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