Water → HCID 68559075, compound

HRID 2362029Notes

Reaction equation

HRID 2362029 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH:5]=[N:6][OH:7].[O:12]1[CH:16]=[CH:15][CH2:14][CH2:13]1.O>C(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[CH:14]3[CH2:15][CH2:16][O:12][CH:13]3[O:7][N:6]=2)[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

6

Reactant 3

HCID 962WaterHCID 709342,3-DihydrofuranHCID 2207415331-92-0

Product 1

HCID 68559075HCID 68559075, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 3,4-dichlorobenzaldehyde oxime (1 eq) in DCM (10 vol) was added a 50% aqueous bleach solution (10 vol). 2,3-Dihydrofuran was then added and the resultant biphasic system was stirred vigorously at room temperature for 21 hours. Water (25 vol) and brine (25 vol) were added and the organic layer was separated. The aqueous phase was further extracted with (2×5 vol) DCM. The combined organic phases were washed with a 1:1 mixture of water and brine (50 vol), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash column chromatography (eluent: EtOAc:heptane) to yield 3-(3,4-Dichloro-phenyl)-3a,4,5,6a-tetrahydro-furo[3,2-d]isoxazole.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous phase was further extracted with (2×5 vol) DCM
  3. washThe combined organic phases were washed with a 1:1 mixture of water and brine (50 vol)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography (eluent: EtOAc:heptane)

Sources & evidence

ORD record
ord-8124340277b9420098a15a906a993914
Source dataset
uspto-grants-2014_04
Patent number
US08691824B2

Reaction notes

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