Toluene → Acetate hexane

HRID 1110370Notes

Reaction equation

HRID 1110370 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6]CC1.CN(C)C=[O:11].[C:13]1(C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Cl-].[Cd+2].[Cl-]>[C:7]([O-:3])(=[O:11])[CH3:6].[CH3:17][CH2:18][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Product 1

HCID 22139250Acetate hexaneYield 47%

Reagents, catalysts & solvents 1

HCID 24633Cadmium chloride, dihydrateCatalyst

Procedure

The procedure used in Example 7a was followed except for the following changes or substitutions: the enamine from Example 44c (1.72 g) was used instead of the enamine in Example 7a; NaH (0.29 g, 55% in oil instead of 0.17 g), tetrahydrofuran (6 ml instead of 2 ml), cadmium chloride (1.34 g instead of 81 g), dimethylformamide (0.5 ml) and toluene (7 ml instead of the amount indicated in Example 7a). After completion of the reaction and isolation of the crude product as described in Example 7a, the product was purified by column chromatography over silica gel using ethyl acetate:hexane (1:3 to 1:1 gradient) as the eluent. There was obtained 0.80 g (47%) of the acetate:hexane (1:1); m.p. 152°-152.5°.

Workup

  1. customthe product was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-439b6e5840f9496ba55b944463c8049a
Source dataset
uspto-grants-1990_12
Patent number
US04975435

Reaction notes

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