Cycloheptanone → 2-[(Tetrahydropyranyloxy)acetyl]cycloheptanone

HRID 1655403

反応式

HRID 1655403 の反応式
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:15][CH2:16][C:17](OCC)=[O:18].[H-].[Na+].[NH4+].[Cl-]>CCOCC.CCO.CO.CCCCCC>[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:15][CH2:16][C:17]([CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:1]1=[O:8])=[O:18]

参加物

9

反応物 4

HCID 10400CycloheptanoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10899396ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate

生成物 1

HCID 149651552-[(Tetrahydropyranyloxy)acetyl]cycloheptanone収率 88.2%

試薬・触媒・溶媒 4

HCID 702Ethanol触媒HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

実験手順

A solution of 2.80 g (25 mmol) of cycloheptanone and 4.71 g (25 mmol) of ethyl (tetrahydropyranyloxy)acetate (Ireland, R. E.; Wipf, P. Tetrahedron Lett., 1989, 30, 919-22) in 20 mL of Et2O was added over the course of 1 h to an ice-cold, stirring mixture of hexane-washed NaH and 0.12 mL (2 mmol, 0.092 g) of absolute EtOH in 10 mL of Et2O under N2. The light brown mixture was allowed to warm to room temperature and was stirred overnight. MeOH (5 mL) was added and the solution was poured onto 200 mL of saturated aqueous NH4Cl. After acidification to pH 2 with 1N aqueous HCl, the mixture was extracted with Et2O. The organic layer was washed with brine, dried over Na2SO4, and concentrated to give 5.61 g of crude 2-[(tetrahydropyranyloxy)acetyl]cycloheptanone as a light brown oil.

後処理

  1. stirringwas stirred overnight
  2. extractionAfter acidification to pH 2 with 1N aqueous HCl, the mixture was extracted with Et2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-80d9958d729141748df57ed9f8ee1dc3
出典データセット
uspto-grants-1993_10
特許番号
US05250561

関連ノート

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