Sulfuric Acid → methyl 2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propanoate

HRID 553615ノート

反応式

HRID 553615 の反応式
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.S(=O)(=O)(O)O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][O:6][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 80803,4-dihydro-2H-pyranHCID 84152Methyl 3-hydroxypivalate

生成物 1

HCID 59253280methyl 2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propanoate収率 117%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 66.3 mL (0.51 mol) of hydroxypivalic acid methyl ester in DCM (325 mL) are added 95.8 mL (1.04 mol) of 3,4-dihydro-2H-pyran. The reaction mixture is cooled to 0° C. and sulfuric acid on silica gel (2.04 g, 0.2 mL sulfuric acid/10 g silica gel) is added and the reaction mixture is stirred at room temperature for 25 minutes. After this time, the reaction mixture is filtered and concentrated under reduced pressure to yield 129 g of 2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propionic acid methyl ester as a yellow oil, which is used in the next step without further purification. Yield: quantitative; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12 (6H, s), 1.13 (6H, s), 1.4-1.7 (6H, m), 3.3 (1H, m), 3.4 (1H, m), 3.6 (3H, s), 3.65 (1H, d), 3.7 (1H, m), 4.55 (1H, t).

後処理

  1. filtrationAfter this time, the reaction mixture is filtered
  2. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ac5bc13311eb4614bc5581c97f4a897e
出典データセット
uspto-grants-2011_11
特許番号
US08048899B2

反応ノート

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