Triphenylphosphine → 3-[3-(3-{3-[2,2,2-Trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propoxy)-phenyl]-propionic acid ethyl ester

HRID 1452689Notes

Reaction equation

HRID 1452689 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[O:21][CH2:22][CH2:23][CH2:24][OH:25])([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:4]([F:7])([F:6])[F:5].[CH2:31]([O:33][C:34](=[O:44])[CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39](O)[CH:38]=1)[CH3:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:31]([O:33][C:34](=[O:44])[CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:25][CH2:24][CH2:23][CH2:22][O:21][C:20]2[CH:26]=[CH:27][CH:28]=[C:18]([C:3]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)([C:4]([F:6])([F:5])[F:7])[C:2]([F:29])([F:30])[F:1])[CH:19]=2)[CH:38]=1)[CH3:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 15197885Ethyl 3-(3-hydroxyphenyl)propanoateHCID 866042193-{3-[2,2,2-Trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propan-1-ol

Product 1

HCID 866042213-[3-(3-{3-[2,2,2-Trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propoxy)-phenyl]-propionic acid ethyl esterYield 59.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

150 mg (0.3 mmol) of 3-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propan-1-ol and 73 mg (0.38 mmol) of 3-(3-hydroxy-phenyl)-propionic acid ethyl ester (CAS 34708-60-6) in 4 mL of THF were treated with 117 mg (0.44 mmol) of triphenylphosphine. The solution was cooled to 0° C. and treated with 88 μL (0.44 mmol) of DIAD. The mixture was stirred at room temperature overnight, the solvent was evaporated and the crude mixture was purified by column chromatography on silica gel with a gradient of EtOAc/n-heptane 1:5 to 1:3 to yield 110 mg (52%) of 3-[3-(3-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-propoxy)-phenyl]-propionic acid ethyl ester as a colorless liquid, MS: 614 (M)+.

Workup

  1. customthe solvent was evaporated
  2. customthe crude mixture was purified by column chromatography on silica gel with a gradient of EtOAc/n-heptane 1:5 to 1:3

Sources & evidence

ORD record
ord-745baa6afce94beb8f57c94b2a0ced01
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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