Boron trifluoride etherate → Spiro(4.5)decan-6-one

HRID 2059745Notes

Reaction equation

HRID 2059745 reaction equation
[C:1]1([OH:12])([C:6]2(O)[CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.COC(OC)OC.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:7]1[C:6]2([CH2:2][CH2:3][CH2:4][CH2:5][C:1]2=[O:12])[CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 9005Trimethyl orthoformateHCID 2917831,1'-Bicyclopentyl-1,1'-diol

Product 1

HCID 290662Spiro(4.5)decan-6-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of bi(cyclopentane)-1,1′-diol (5.16 g, 29.4 mmol) in CH2Cl2 (80 mL), cooled to −20° C., was added trimethoxymethane (3.22 mL, 29.4 mmol), followed by boron trifluoride etherate (2.98 mL, 23.52 mmol). The cold bath was removed, and the reaction was stirred at ambient temperature for 2 hours. The mixture was then diluted with CH2Cl2 (100 mL), washed with saturated NaHCO3, dried with MgSO4, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel (100% hexane to 15:85 EtOAc/hexane, eluant) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 2.40 (t, 2H), 2.00-2.11 (m, 2 H), 1.78-1.87 (m, 2 H), 1.71 (t, 4H), 1.59 (t, 4H), 1.39 (t, 2 H). MS (DCI+) m/z 153 (M+H).

Workup

  1. customThe cold bath was removed
  2. additionThe mixture was then diluted with CH2Cl2 (100 mL)
  3. washwashed with saturated NaHCO3
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was chromatographed on silica gel (100% hexane to 15:85 EtOAc/hexane, eluant)

Sources & evidence

ORD record
ord-cd9efb9fbd3e400e8c7da46f9d5d819d
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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