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

HRID 369541Notes

Reaction equation

HRID 369541 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-750f735f4a274cb1b0de79dfb5398fd1
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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