Cycloheptanone → 2-[(Tetrahydropyranyloxy)acetyl]cycloheptanone

HRID 1034350

반응식

HRID 1034350 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

HCID 149651552-[(Tetrahydropyranyloxy)acetyl]cycloheptanone수율 88.2%

시약·촉매·용매 4

HCID 702Ethanol촉매HCID 887Methanol용매HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0fc612491b464df2ad9d3ebe63f66487
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05315012

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