Hydrochloric Acid → 2-Chloro-1-(oxolan-3-yl)ethanone

HRID 376577

Reaction equation

HRID 376577 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.C(Cl)(=O)[C:10]([Cl:12])=O.[N+](=C)=[N-].Cl>ClCCl.CCOCC>[Cl:12][CH2:10][C:6]([CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 65578Oxalyl chlorideHCID 4661317(R)-Tetrahydro-3-furoic acid

Product 1

HCID 187800522-Chloro-1-(oxolan-3-yl)ethanoneYield 88.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

(RS)-3-Tetrahydrofuroic acid (3.48g) in dichloromethane (40ml) was treated with oxalyl chloride (11.43g) as described in Example 1(a). The resultant acid chloride in dichloromethane (40ml) was then treated with excess diazomethane (60mM) in ether (100ml), followed by hydrogen chloride. The solution was washed once with brine, dried and concentrated. Flash chromatography on silica gel, eluting with 40% ethyl acetate/hexane afforded the title compound as a pale yellow oil, (3.924g, 88%); vmax (CH2Cl2) 1735 and 1716cm-1 ; 2.17 (2H, dt, J 7.0, 7.5Hz), 3.47-3.58 (1H, m), 3.77-4.04 (4H, m) and 4.18 (2H, s); [mass spectrum: +ve ion (ammonia) MNH4+ (166)].

Workup

  1. washThe solution was washed once with brine
  2. customdried
  3. concentrationconcentrated
  4. washFlash chromatography on silica gel, eluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6078964c5528424784040ce3217f6797
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Linked notes

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