Cycloheptanone → Spiro(5.6)dodecan-7-one

HRID 2059758

반응식

HRID 2059758 반응식
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].Cl[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]I>C1COCC1.CCOCC>[CH2:16]1[C:2]2([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:1]2=[O:8])[CH2:20][CH2:19][CH2:18][CH2:17]1

참가 물질

6

반응물 3

HCID 10400CycloheptanoneHCID 1089141-Chloro-5-iodopentaneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 282264Spiro(5.6)dodecan-7-one

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of cycloheptanone (2.1 mL, 17.83 mmol) and potassium tert-butoxide (2.60 g, 23.18 mmol) in THF (10 mL) was dropwise added a solution of 1-chloro-5-iodopentane (2.74 mL, 19.61 mmol) in THF (10 mL). The mixture was stirred at ambient temperature for 16 hours. It was then diluted with ether (200 mL), washed with saturated NH4Cl and brine, dried with MgSO4, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel (95:5 hexane-EtOAc, eluant) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 2.50 (t, 2 H), 1.55-1.79 (m, 8 H), 1.30-1.52 (m, 10 H). MS (DCI+) m/z 198 (M+H).

후처리

  1. washwashed with saturated NH4Cl and brine
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was chromatographed on silica gel (95:5 hexane-EtOAc, eluant)

출처 및 근거

ORD 기록
ord-bf9988580cb643218680808d7885e49f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278313B2

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