Benzene → 2-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]-1-(3-methylphenyl)ethanol

HRID 1901186Notes

Reaction equation

HRID 1901186 reaction equation
N[CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1)[OH:4].O=[C:13]([CH3:27])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:26][O:25][C:23]([CH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH:13]([CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=2)[OH:4])[CH3:27])=[CH:21][CH:20]=1)=[O:24]

Participants

6

Reactant 4

HCID 241BenzeneHCID 5003444Sodium cyanoborohydrideHCID 134825112-Amino-1-(3-methylphenyl)ethan-1-olHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Product 1

HCID 233706802-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]-1-(3-methylphenyl)ethanolYield 56.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 3, but using 2.5 g of 2-amino-1-(3-methylphenyl)ethanol (prepared as described in Preparation 44), 4.4 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 80 ml of benzene, 60 ml of absolute methanol and 4.5 g of sodium cyanoborohydride, and then purifying the reaction product by column chromatography through silica gel, using ethyl acetate as the eluent, 3.2 g of the title compound were obtained having an Rf=0.24 (thin layer chromatography over silica gel, using ethyl acetate as the developing solvent).

Workup

  1. custompurifying the reaction product by column chromatography through silica gel

Sources & evidence

ORD record
ord-4c85f35d95584c3394a1f9941c637b83
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

Loading…