3,5-Heptanedione → HCID 22005256, 화합물

HRID 324891노트

반응식

HRID 324891 반응식
[CH3:1][C:2]([O:5][C:6]([CH2:8][C:9]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:10])=[O:7])([CH3:4])[CH3:3].[CH3:19][CH2:20][C:21](=O)[CH2:22][C:23](=O)[CH2:24][CH3:25].C[O-].[Na+]>CO>[CH2:20]([C:21]1[CH:22]=[C:23]([CH2:24][CH3:25])[C:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[C:9]([OH:10])[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH3:19]

참가 물질

5

반응물 3

HCID 819233,5-HeptanedioneHCID 119788Bis(1,1-dimethylethyl) 3-oxoglutarateHCID 10942334Sodium Methoxide

생성물 1

HCID 22005256HCID 22005256, 화합물수율 97.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of di-tert-butyl 1,3-acetonedicarboxylate (10 g, 38.7 mmol), 3,5-heptanedione (6.5 g, 50.3 mmol) and sodium methoxide (2.7 g, 50.3 mmol) in methanol (100 mL) was stirred at room temperature overnight. Methanol was removed via rotary evaporation and the resulting orange sludge was partitioned between diethyl ether (100 mL) and 10% aqueous hydrochloric acid (100 mL). The separated aqueous layer was extracted with diethyl ether (50 mL×2). The combined organic portions were washed with saturated aqueous sodium chloride (20 mL), dried over sodium sulfate, filtered through a pad of silica (20 mm×40 mm) and concentrated in vacuo to yield a yellow oil (13.23 g, 97%): 1H NMR (300 MHz, CDCl3): δ 1.20 (t, 6H), 1.60 (s, 18H) 2.74 (q, 4H), 6.55 (s, 1H), 11.73 (s, 1H).

후처리

  1. customMethanol was removed via rotary evaporation
  2. customthe resulting orange sludge was partitioned between diethyl ether (100 mL) and 10% aqueous hydrochloric acid (100 mL)
  3. extractionThe separated aqueous layer was extracted with diethyl ether (50 mL×2)
  4. washThe combined organic portions were washed with saturated aqueous sodium chloride (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered through a pad of silica (20 mm×40 mm)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ae61b28b19e14a8ba073f2fd1cddf87a
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218431B1

반응 노트

불러오는 중…