Hydrochloric Acid → 4-cyano-4-(3-iodophenyl)-3,4,5,6-tetrahydro-2H-pyran

HRID 1108105Notes

Reaction equation

HRID 1108105 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Cl.Cl>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.[OH-].[Na+]>[C:9]([C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)#[N:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8115Bis(2-chloroethyl) etherHCID 27593682-(3-Iodophenyl)acetonitrile

Product 1

HCID 117713774-cyano-4-(3-iodophenyl)-3,4,5,6-tetrahydro-2H-pyranYield 76%

Reagents, catalysts & solvents 2

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3-iodophenylacetonitrile (2.43 g, 10 mmol), bis-(2-chloroethyl)ether (1.57 g, 11 mmol), hexadecyltributylphosphonium bromide (250 mg, 0.5 mmol) and 50% aqueous sodium hydroxide (20 ml) was stirred vigorously for 1 h at room temperature. The mixture was neutralized with 6 N aqueous HCl, transferred to a separatory funnel and extracted with ethyl acetate (50 ml×3). The combined extracts were washed with 2 N aqueous HCl (50 ml), water (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo. The residual crude solids were collected and washed with cold Et2O (30 ml) to afford 2.38 g (76%) of the titled compound as white solids.

Workup

  1. customtransferred to a separatory funnel
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. washThe combined extracts were washed with 2 N aqueous HCl (50 ml), water (50 ml) and brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residual crude solids were collected
  7. washwashed with cold Et2O (30 ml)

Sources & evidence

ORD record
ord-4d608d88aa9140eaa16163edcf9e2f69
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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