Methyl 4-(octadecyloxy)benzoate → (S)-Methyl-4'-(1-methylnonyloxy)-3'-(nitro)-4-biphenylcarboxylate

HRID 413638Notes

Reaction equation

HRID 413638 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=2)=[CH:19][CH:18]=1)=[O:16].COC(=O)C1C=CC(O[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]CCCCCCCC)=CC=1>CCOCC>[CH3:13][O:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C@@H:44]([CH3:43])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=2)=[CH:21][CH:22]=1)=[O:16]

Participants

5

Reactant 3

HCID 4189536Methyl 4-(octadecyloxy)benzoateHCID 5462977Diethyl azodicarboxylateHCID 185210364-(4-Methoxycarbonylphenyl)-2-nitrophenol

Product 1

HCID 54059652(S)-Methyl-4'-(1-methylnonyloxy)-3'-(nitro)-4-biphenylcarboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

DEAD (323 mg, 1.85 mmol), phenol 40 (440 mg, 1.61 mmol), R-2-decanol (268 mg, 1.69 mmol), and TPP (486 mg, 1.85 mmol) in 16 ml anhydrous ether were reacted according to the procedure for compound 35a. The crude product was concentrated and purified via flash chromatography over silica gel with gradual elutions from 95/5 to 65/35 (Hex/EtOAc). Evaporation of the solvent yielded 439 mg (66%) of a yellow solid.

Workup

  1. concentrationThe crude product was concentrated
  2. custompurified via flash chromatography over silica gel with gradual elutions from 95/5 to 65/35 (Hex/EtOAc)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c9c619bc533e49f0bdb60336e8a02e69
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Reaction notes

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