Water → 4,4-Dimethyl-pent-2-enoic acid methyl ester

HRID 15281

反応式

HRID 15281 の反応式
C(OP([CH2:9][C:10]([O:12][CH3:13])=[O:11])(OCC)=O)C.[Li]CCCC.[CH3:19][C:20]([CH3:24])([CH3:23])[CH:21]=O.O>C1COCC1>[CH3:13][O:12][C:10](=[O:11])[CH:9]=[CH:19][C:20]([CH3:24])([CH3:23])[CH3:21]

参加物

6

反応物 4

HCID 962WaterHCID 12417PivalaldehydeHCID 66113Methyl diethylphosphonoacetateHCID 178418339Butyllithium

生成物 1

HCID 5582314,4-Dimethyl-pent-2-enoic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Methyl diethylphosphonoacetate (13.35 mL, 73.6 mmol, 1.05 eq.) was dissolved in THF (30 mL) and cooled to −78° C. in an acetone-dry ice bath. n-BuLi (1.6M in hexanes) (45.8 mL, 73.2 mmol, 1.05 eq.) was added slowly over 20 min. Trimethylacetaldehyde (6.0 g, 69.6 mmol, 1.0 eq.), was added to the reaction and allowed to stir at −78° C. for 20 minutes and warmed to room temperature and stirred overnight. Water (30 mL) was added to quench and extracted with ethyl ether (3×100 mL). The combined organics were washed with brine and dried over MgSO4, filtered and evaporated to provide 4,4-Dimethyl-pent-2-enoic acid methyl ester, a colorless liquid (8.52 g, 60.0 mmol, 86%) and was used directly in the next reaction. 1H NMR (CDCl3, 400 MHz) δ 0.89 (s, 9H), 3.64 (s, 3H), 5.64 (d, 1H, J=16.0 Hz), 6.88 (d, 1H, J=16.0 Hz).

後処理

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. customto quench
  4. extractionextracted with ethyl ether (3×100 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-1899fb5ed01e4b20849c347516781011
出典データセット
uspto-grants-2010_06
特許番号
US07732449B2

関連ノート

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