2-(2-(3-Methoxyphenyl)ethyl)phenol → HCID 53745428, compound

HRID 743281Notes

Reaction equation

HRID 743281 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:7][CH:8]=1.[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH2:30]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:24])([CH3:21])([CH3:20])[CH3:19].CC(C)([O-])C.[K+]>CC(N(C)C)=O>[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH2:30][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 105854482-(2-(3-Methoxyphenyl)ethyl)phenolHCID 11783214tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 53745428HCID 53745428, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 40(a), 2.00 g of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 20), 3.74 g of (S)-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine and 0.983 g of potassium t-butoxide were reacted in 20 ml of dimethylacetamide. The mixture was then worked up as described in Example 40(a), and the crude product thus obtained was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.65 g (yield 45%) of the title compound as a colorless oil.

Workup

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-eff72ecf09ee44c7a9b0e6c83d6db2e4
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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