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

HRID 2386991Notes

Reaction equation

HRID 2386991 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 methylene chloride (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 methylene chloride (100 mL), washed with saturated sodium bicarbonate, dried with magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel (100% hexane to 15:85 ethyl acetate/hexane, eluant) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 2.40 (t, 2H), 2.00-2.11 (m, 2H), 1.78-1.87 (m, 2H), 1.71 (t, 4H), 1.59 (t, 4H), 1.39 (t, 2H); MS (DCI+) m/z 153 (M+H)+.

Workup

  1. customThe cold bath was removed
  2. additionThe mixture was then diluted with methylene chloride (100 mL)
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was chromatographed on silica gel (100% hexane to 15:85 ethyl acetate/hexane, eluant)

Sources & evidence

ORD record
ord-abf770cb49634017b98a7c6ca2d8c014
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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