Methanol → Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl ester

HRID 1292957

反応式

HRID 1292957 の反応式
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Li+].[CH2:8]1[O:18][C:11]2([CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)[O:10][CH2:9]1.C[OH:20]>O>[O:10]1[C:11]2([CH2:16][CH2:15][C:14](=[CH:2][C:3]([O:4][CH2:5][CH3:1])=[O:20])[CH2:13][CH2:12]2)[O:18][CH2:8][CH2:9]1

参加物

6

反応物 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 62714Lithium hydrideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

生成物 1

HCID 373318Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl ester収率 93%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of THF (18 mL) under argon was added 0.38 g (47.8 mmol, 5 equiv) of LiH, followed by slow addition of 8.78 g (47.8 mmol, 5 equiv) of triethyl phosphonoacetate. The solution was stirred at rt for 1 h and 1.49 g (9.6 mmol, 1 equiv) of 1,4-cyclohexanedione mono-ethylene ketal was added and the solution was heated at 65° C. for 16 h. Upon cooling the solution was treated with MeOH (10 mL) and water (5 mL) and concentrated in vacuo. The resulting yellow oil was purified by silica gel chromatography eluting with 4:1 Hex/EtOAc to yield 1.89 g (93%) of a clear oil. 1H-NMR (CDCl3-d) δ 5.67 (s, 1H), 4.16 (t, 2H), 3.99 (m, 4H), 3.02 (m, 2H), 2.39 (m, 2H), 1.78 (m, 4H), 1.29 (t, 3H); LCMS RT=2.56 min; [M+H]+=226.9.

後処理

  1. temperaturethe solution was heated at 65° C. for 16 h
  2. temperatureUpon cooling the solution
  3. concentrationconcentrated in vacuo
  4. customThe resulting yellow oil was purified by silica gel chromatography
  5. washeluting with 4:1 Hex/EtOAc

出典と根拠

ORDレコード
ord-ddeb1a6f4b9744bf933637a33a3216f9
出典データセット
uspto-grants-2007_07
特許番号
US07238701B2

関連ノート

読み込み中…