Cycloheptanone → Spiro(5.6)dodecan-7-one

HRID 2059758

Reaction equation

HRID 2059758 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 282264Spiro(5.6)dodecan-7-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-bf9988580cb643218680808d7885e49f
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Linked notes

Loading…