Cycloheptanone → Spiro(5.6)dodecan-7-one

HRID 2059758

反応式

HRID 2059758 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 282264Spiro(5.6)dodecan-7-one

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bf9988580cb643218680808d7885e49f
出典データセット
uspto-grants-2012_10
特許番号
US08278313B2

関連ノート

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