Sodium hydride → 2-(2-Methyl-allyloxy)-pent-4-enoic acid ethyl ester

HRID 1808004노트

반응식

HRID 1808004 반응식
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:12])[CH:7]([OH:11])[CH2:8][CH:9]=[CH2:10])[CH3:4].Br[CH2:14][C:15]([CH3:17])=[CH2:16]>C1COCC1>[CH2:3]([O:5][C:6](=[O:12])[CH:7]([O:11][CH2:16][C:15]([CH3:17])=[CH2:14])[CH2:8][CH:9]=[CH2:10])[CH3:4]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 3577853-Bromo-2-methyl-1-propeneHCID 10986362ethyl 2-hydroxypent-4-enoate

생성물 1

HCID 597523452-(2-Methyl-allyloxy)-pent-4-enoic acid ethyl ester수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a cold (0° C.) stirred suspension of NaH (55% dispersion in oil, 227.9 mg, 5.2 mmol, 1.3 eq) in THF (20 mL) was added drop wise a solution of 2-hydroxy-pent-4-enoic acid ethyl ester (0.576 g, 4.0 mmol) in THF (20 mL) and stirred for 1 h. The reaction mixture was then treated with 3-bromo-2-methylpropene (0.81 g, 6.0 mmol, 0.61 mL), slowly warmed up to rt, and stirred for 1 h. It was carefully quenched with saturated NH4Cl solution. Reaction mixture was extracted with EtOAc (3×20 mL) organic solution was washed with brine, dried (Na2SO4), concentrated. Purification of the residue on silica gel column chromatography using 5% EtOAc-Hexane furnished 2-(2-methyl-allyloxy)-pent-4-enoic acid ethyl ester (0.521 g, 66%) as oil.

후처리

  1. stirringstirred for 1 h
  2. temperatureslowly warmed up to rt
  3. stirringstirred for 1 h
  4. customIt was carefully quenched with saturated NH4Cl solution
  5. customReaction mixture
  6. extractionwas extracted with EtOAc (3×20 mL) organic solution
  7. washwas washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customPurification of the residue on silica gel column chromatography

출처 및 근거

ORD 기록
ord-3980e6e15dec443680c99ed38b5a74b0
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357718B2

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