Acetic acid--water (1/1) → 7-Oxaspiro[3.5]nonan-2-one

HRID 1853073Notes

Reaction equation

HRID 1853073 reaction equation
Cl[C:2]1(Cl)[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:4][C:3]1=[O:11].C(O)(=O)C.O>CCOCC.[Zn]>[CH2:4]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:2][C:3]1=[O:11]

Participants

5

Reactant 2

HCID 21899381Acetic acid--water (1/1)HCID 866853361,1-Dichloro-7-oxaspiro[3,5]nonan-2-one

Product 1

HCID 674519097-Oxaspiro[3.5]nonan-2-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Procedure

The impure 1,1-dichloro-7-oxaspiro[3.5]nonan-2-one from Step B was stirred with zinc (150 mg; 2.30 mmol) and 5 mL of acetic acid/water (1:1) for 4 hours. The mixture was stored at −20° C. for 1 day, diluted with ether (20 mL) and filtered through a pad of Celite®. The solution was neutralized with aqueous sodium bicarbonate solution and extracted into ether (5×20 mL). The combined ether extracts were dried (sodium sulfate), filtered and concentrated under reduced pressure. The material was purified by chromatography on silica gel, eluting with 1:1 ethyl acetate/hexane to give the product as a colorless oil (61 mg).

Workup

  1. filtrationfiltered through a pad of Celite®
  2. extractionextracted into ether (5×20 mL)
  3. dry with materialThe combined ether extracts were dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe material was purified by chromatography on silica gel
  7. washeluting with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-fb38331038d7430397d7267b8568337c
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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