Ethylparaben → HCID 65018987, 화합물

HRID 452865노트

반응식

HRID 452865 반응식
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.O[CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:17]1[CH2:18][CH2:19][CH:14]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[CH2:15][CH2:16]1

참가 물질

6

반응물 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 75555Diisopropyl diazene-1,2-dicarboxylate

생성물 1

HCID 65018987HCID 65018987, 화합물수율 61.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

An ice-cold solution of ethyl 4-hydroxybenzoate (0.82 g), 4-hydroxy-tetrahydro-2H-pyran (0.5 g) and triphenylphosphine in THF (50 ml) was treated dropwise with diisopropyl azodicarboxylate (1.69 ml). After 15 min the cooling bath was removed and the reaction stood overnight at rt. The mixture was evaporated, redissolved in toluene and successively washed with 2N sodium hydroxide (2×20 ml), water (2×20 ml) and brine (20 ml). After drying (magnesium sulfate) the solution was loaded directly on to a silica flash column (step gradient 10-30% EtOAc in light petroleum 40-60) to give the title compound (D5) (0.75 g). 1H NMR δ (CDCl3): 7.98 (2H, d, J=8.5 Hz), 6.91 (2H, d, J=8.5 Hz), 4.60 (1H, m), 4.35 (2H, q, J=9.8 Hz), 3.98 (2H, m), 3.57 (2H, m), 2.05 (2H, m), 1.80 (2H, m), 1.38 (3H, t, J=9.8 Hz).

후처리

  1. customAfter 15 min the cooling bath was removed
  2. customThe mixture was evaporated
  3. dissolutionredissolved in toluene
  4. washsuccessively washed with 2N sodium hydroxide (2×20 ml), water (2×20 ml) and brine (20 ml)
  5. dry with materialAfter drying (magnesium sulfate) the solution

출처 및 근거

ORD 기록
ord-7f3e6601f8844770b94f6251042ca325
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492375B2

반응 노트

불러오는 중…