3,5-Heptanedione → HCID 22005256、化合物

HRID 324891ノート

反応式

HRID 324891 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 22005256HCID 22005256、化合物収率 97.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ae61b28b19e14a8ba073f2fd1cddf87a
出典データセット
uspto-grants-2001_04
特許番号
US06218431B1

反応ノート

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