N-methoxy-N-methylcyclohexanecarboxamide → 6-Cyclohexanecarbonyl-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

HRID 2251598Notes

Reaction equation

HRID 2251598 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]([OH:25])=[O:24])[C:5]2[O:9][C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1.O(C)[Li].CON(C)[C:32]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:33]>>[CH:34]1([C:32]([C:2]2[CH:3]=[C:4]([C:23]([OH:25])=[O:24])[C:5]3[O:9][C:8]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[O:7][C:6]=3[CH:22]=2)=[O:33])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 3

HCID 11769007N-methoxy-N-methylcyclohexanecarboxamideHCID 596429946-Bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acidHCID 178419045HCID 178419045, compound

Product 1

HCID 596430196-Cyclohexanecarbonyl-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

Procedure

6-Bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid (1.26 g, 3.16 mmol, 1 eq.), LiOMe (240 mg, 6.32 mmol, 2 eq.) and cyclohexanecarboxylic acid methoxy-methyl-amide (650 mg, 3.8 mmol, 1.2 eq.) as the electrophile were reacted according to GP4, Method A. The crude product was purified using flash chromatography (silica gel, hexane/Et2O/AcOH 5:1:0.1) and subsequent recrystallization from CH2Cl2/hexane to give the title compound as a yellowish solid.

Workup

  1. customThe crude product was purified
  2. customflash chromatography (silica gel, hexane/Et2O/AcOH 5:1:0.1) and subsequent recrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-5ad24b2c567b4cb59a0a7b228c405e32
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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