Lithium Hydroxide → ({[2-(4-Methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid

HRID 254087ノート

反応式

HRID 254087 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:17][S:18][CH2:19][C:20]([O:22]CC)=[O:21])[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[CH:5][CH:4]=1.[Li+].[OH-]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:17][S:18][CH2:19][C:20]([OH:22])=[O:21])[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 86619088Ethyl ({[2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate

生成物 1

HCID 66842966({[2-(4-Methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid収率 98.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

Ethyl ({[2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate (5.95 g, 16.8 mmol) was dissolved in THP (75 ml) and cooled to 0° C. LiOH (2.11 g, 50.4 mmol) in water (40 ml) was added and the mixture was stirred for 90 minutes. Water was added and the mixture was extracted twice with diethyl ether. The aqueous layer was acidified using 2M HCl until pH=4 and extracted twice with CH2Cl2. The combined CH2Cl2 layers were dried (Na2SO4) and concentrated under reduced pressure to afford 5.4 g (>98%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.4 (s, 3H), 3.0 (s, 2H), 3.4 (s, 2H), 3.5 (s, 4H), 3.9 (s, 3H), 6.9 (d, 2H), 7.4 (d, 2H).

後処理

  1. extractionthe mixture was extracted twice with diethyl ether
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe combined CH2Cl2 layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-8909f83d352d401cbbb6872adefa3786
出典データセット
uspto-grants-2011_01
特許番号
US07871998B2

反応ノート

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