Triphenylphosphine → 3-{4-[2-(4-Benzyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester

HRID 987251Notes

Reaction equation

HRID 987251 reaction equation
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH2:19]([O:21][C:22](=[O:35])[CH:23]([O:32][CH2:33][CH3:34])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[CH3:20].[CH2:36]([O:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50][CH2:51]O)=[CH:46][CH:45]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:19]([O:21][C:22](=[O:35])[CH:23]([O:32][CH2:33][CH3:34])[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:31][CH2:51][CH2:50][C:47]2[CH:48]=[CH:49][C:44]([O:43][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:45][CH:46]=2)=[CH:29][CH:30]=1)[CH3:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 3017260p-(Benzyloxy)phenethyl alcoholHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 537559633-{4-[2-(4-Benzyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Azodicarbonyl dipiperidine (7.5 g; 30 mmole) was added to 2-ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (described in Example 20b) (7 g; 30 mmole), 2-(4-benzyloxyphenyl)ethanol (6.8 g; 30 mmole) and triphenylphosphine (7.8 g; 30 mmole) dissolved i dichloromethane. After stirring at room temperature overnight the solvent was evaporated in vacuo and diethyl ether was added. The solid material was filtered off after 1 hour and the filtrate was evaporated in vacuo. Purification by chromatography on silica gel using ethyl acetate:dichloromethane as eluant gave 10 g (yield 75%) of 3-{4-[2-(4-benzyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester.

Workup

  1. customwas evaporated in vacuo and diethyl ether
  2. additionwas added
  3. filtrationThe solid material was filtered off after 1 hour
  4. customthe filtrate was evaporated in vacuo
  5. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-d5a22a224eec4eff9e28778563af7857
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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