Bis(2-chloroethyl) ether → (2SR, 4RS)-4-cyano-4-(3-iodophenyl)-2-methyl-3,4,5,6-tetrahydro-2H-pyran

HRID 1418492Notes

Reaction equation

HRID 1418492 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.I[CH2:12][CH:13]([O:15][CH2:16][CH2:17]I)[CH3:14].FC1C=C(CC#N)C=C(F)C=1.ClCCOCCCl>>[C:9]([C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=2)[CH2:17][CH2:16][O:15][CH:13]([CH3:14])[CH2:12]1)#[N:10]

Participants

5

Reactant 4

HCID 8115Bis(2-chloroethyl) etherHCID 5185653,5-DifluorophenylacetonitrileHCID 27593682-(3-Iodophenyl)acetonitrileHCID 187863711-Iodo-2-(2-iodoethoxy)propane

Product 1

HCID 18786332(2SR, 4RS)-4-cyano-4-(3-iodophenyl)-2-methyl-3,4,5,6-tetrahydro-2H-pyran

Procedure

The titled compounds were prepared according to the procedure described in Example 25A except that 3-iodophenyacetonitrile and 1-iodo-2-(2-iodoethoxy)propane were used in place of 3,5-difluorophenylacetonitrile and bis-(2chloroethyl)ether. The diastereomers were separated by silica gel column chromatography to afford 1.46 g (38%) of a less polar isomer, (2SR, 4RS)-4-cyano-4-(3-iodophenyl)-2-methyl-3,4,5,6-tetrahydr o-2H-pyran; and 1.31 g (34%) of a more polar isomer, (2SR, 4SR)-4-cyano-4-(3-iodophenyl)-2-methyl-3,4,5,6-tetrahydro-2H-pyran.

Workup

  1. customThe diastereomers were separated by silica gel column chromatography

Sources & evidence

ORD record
ord-b51f586578624bfebc863c0855ef8755
Source dataset
uspto-grants-1999_03
Patent number
US05883106

Reaction notes

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