Triphenylphosphine → Ethyl 3-oxo-4-(triphenyl-lambda~5~-phosphanylidene)butanoate

HRID 1942577노트

반응식

HRID 1942577 반응식
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:21][C:22](=[O:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1COCC1.O>[O:29]=[C:22]([CH:21]=[P:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 69484Ethyl 4-chloroacetoacetate

생성물 1

HCID 2734128Ethyl 3-oxo-4-(triphenyl-lambda~5~-phosphanylidene)butanoate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

triphenylphosphine (30.0 g, 114.3 mmol) is added, at ambient temperature, to a solution of commercial ethyl 4-chloro-3-oxobutanoate (18.81 g, 114.3 mmol) in 200 mL of anhydrous THF. The reaction medium is taken to reflux for 18 h before being concentrated under vacuum. The oil obtained is taken up in distilled water then washed with ether. The aqueous phase is then basified by a saturated aqueous solution of NaHCO3 (up to pH 8). After extraction with AcOEt, the organic phases are combined, dried over MgSO4, filtered then concentrated under vacuum. Purification is carried out by recrystallization from ether in order to produce, after filtration and drying, compound 5′-2 (14.96 g, 38.0 mmol, 34%) in the form of a slightly yellow solid.

후처리

  1. temperatureto reflux for 18 h
  2. concentrationbefore being concentrated under vacuum
  3. customThe oil obtained
  4. washthen washed with ether
  5. extractionAfter extraction with AcOEt
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthen concentrated under vacuum
  9. customPurification
  10. customis carried out by recrystallization from ether in order
  11. customto produce
  12. filtrationafter filtration
  13. customdrying

출처 및 근거

ORD 기록
ord-04ebc7b476524b1bb2e31b66601f3e78
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389569B2

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