Benzoyl chloride, 3,4,5-trimethoxy- → HCID 20368522, compound

HRID 616650Notes

Reaction equation

HRID 616650 reaction equation
[C:1]1([CH:7]([CH:13]([N:15]([CH3:17])[CH3:16])[CH3:14])[C:8](OCC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:29]([Cl:31])=[O:30]>>[ClH:31].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:29]([O:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:13]([N:15]([CH3:17])[CH3:16])[CH3:14])=[O:30]

Participants

4

Reactant 3

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 20368524HCID 20368524, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20368522HCID 20368522, compound

Procedure

The title compound is prepared from ethyl 2-phenyl-3-dimethylaminobutyrate and lithium aluminum hydride according to the procedure of Example 2 followed by reaction with 3,4,5-trimethoxybenzoyl chloride according to the procedure of Example 3. Fractional crystallization from isopropanol gives the β-isomer as the main product. It melts at 165°-166° C.

Workup

  1. customFractional crystallization from isopropanol
  2. customgives the β-isomer as the main product

Sources & evidence

ORD record
ord-189d883246374430992f2117e2cdeb49
Source dataset
uspto-grants-1978_02
Patent number
US04075241

Reaction notes

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