Tetrahydrofuran → 2-(Isochroman-1-yl)-2-methylpropionic acid

HRID 1417811노트

반응식

HRID 1417811 반응식
[OH-].[Na+].C1COCC1.[CH:8]1([C:18]([CH3:24])([CH3:23])[C:19]([O:21]C)=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][O:9]1>C(O)C>[CH:8]1([C:18]([CH3:24])([CH3:23])[C:19]([OH:21])=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][O:9]1

참가 물질

5

반응물 3

HCID 8028Tetrahydrofuran2회HCID 14798Sodium Hydroxide2회HCID 23288833Methyl 2-(isochroman-1-yl)-2-methylpropionate

생성물 1

HCID 232888942-(Isochroman-1-yl)-2-methylpropionic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Sodium hydroxide (1N, 12 ml) is added dropwise over several minutes, followed by a few mls of THF (to aid in solution) to a mixture of methyl 2-(isochroman-1-yl)-2-methylpropionate (LXXI, 1.833 g, 7.8 mmol) in ethanol (12 ml). The mixture is stirred overnight at 20°-25°, then at 47° for 2 hr, followed by stirring at 20°-25° over the weekend. Additional THF and sodium hydroxide (1N, 12 ml) are added and the mixture is stirred overnight at 20°-25° and then at 40° for 7 hr, followed by overnight at 20°-25°. Ethanol is then removed under reduced pressure and the resulting solids are dissolved in water. The aqueous phase is separated and washed twice with hexane to remove any unreacted starting material and the aqueous phase is then cooled in an ice/water bath and hydrochloric acid (4N, 6 ml) is added dropwise. The mixture is extracted three times with ether and the combined organic phases are backwashed with saline, dried over magnesium sulfate, and concentrated. Recrystallization from dichloromethane/hexane gives 2-(isochroman-1-yl)-2-methylpropionic acid (LXXII), mp 110.5°-115.75°.

후처리

  1. waitat 47° for 2 hr
  2. stirringby stirring at 20°-25° over the weekend
  3. stirringthe mixture is stirred overnight at 20°-25°
  4. waitat 40° for 7 hr
  5. waitfollowed by overnight at 20°-25°
  6. customEthanol is then removed under reduced pressure
  7. dissolutionthe resulting solids are dissolved in water
  8. customThe aqueous phase is separated
  9. washwashed twice with hexane
  10. customto remove
  11. temperaturethe aqueous phase is then cooled in an ice/water bath
  12. additionhydrochloric acid (4N, 6 ml) is added dropwise
  13. extractionThe mixture is extracted three times with ether
  14. dry with materialdried over magnesium sulfate
  15. concentrationconcentrated
  16. customRecrystallization from dichloromethane/hexane

출처 및 근거

ORD 기록
ord-dcd6aae5780742c4b2f76a5527c64ddd
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877317

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