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

HRID 2249955

반응식

HRID 2249955 반응식
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]

참가 물질

6

반응물 4

HCID 962WaterHCID 12417PivalaldehydeHCID 66113Methyl diethylphosphonoacetateHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-85b27f4924e44d67b96575129df8651b
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07314872B2

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