Hexylene Glycol → 1-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-cyclopropanecarboxylic acid ethyl ester

HRID 512132

反応式

HRID 512132 の反応式
[CH2:1]([O:3][C:4]([C:6]1([C:9]#[N:10])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:11][C:12](O)([CH2:14][CH:15]([OH:17])[CH3:16])[CH3:13]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[O:17][CH:15]([CH3:16])[CH2:14][C:12]([CH3:13])([CH3:11])[N:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 7870Hexylene GlycolHCID 380810Ethyl 1-cyanocyclopropanecarboxylate

生成物 1

HCID 151932001-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-cyclopropanecarboxylic acid ethyl ester収率 61,730.301%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

To concentrated sulfuric acid (102 mL) was added 1-cyano-cyclopropanecarboxylic acid ethyl ester (60 g, 0.43 mol) dropwise followed by 2-methylpentan-2,4-diol (52 g, 0.44 mmol) dropwise at 0° C. The mixture was stirred for an additional 1 h at 0° C. then poured onto ice-water. The aqueous phase was washed with AcOEt (3×200 mL) and then basified to pH 12 with 10 M NaOH. The resulting mixture was extracted with EtOAc (3×500 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel to give 1-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-cyclopropanecarboxylic acid ethyl ester (65 g, yield: 63.2%). 1H NMR (CDCl3 400 MHz): δ4.21-4.06 (m, 3H), 1.73-1.69 (m, 1H), 1.40-1.10 (m, 17H).

後処理

  1. additionthen poured onto ice-water
  2. washThe aqueous phase was washed with AcOEt (3×200 mL)
  3. extractionThe resulting mixture was extracted with EtOAc (3×500 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-70ce7543b46a475e9dd886e37ebb2344
出典データセット
uspto-grants-2015_08
特許番号
US09102591B2

関連ノート

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