Triphenylphosphine → 3-[4-(3,3-Diphenyl-propoxy)-phenyl]-2-ethoxy-propionic acid ethyl ester

HRID 488433Notes

Reaction equation

[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:36]([O:38][C:39](=[O:52])[CH:40]([O:49][CH2:50][CH3:51])[CH2:41][C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)[CH3:37].CCOC(/N=N/C(OCC)=O)=O>>[CH2:36]([O:38][C:39](=[O:52])[CH:40]([O:49][CH2:50][CH3:51])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:10][CH2:9][CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:44][CH:43]=1)[CH3:37]

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 299083,3-Diphenylpropanol

HCID 5462977Diethyl azodicarboxylate

HCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 542575543-[4-(3,3-Diphenyl-propoxy)-phenyl]-2-ethoxy-propionic acid ethyl esterYield 55.5%

Procedure

Reaction of 3,3-diphenyl-propan-1-ol (110 mg, 0.5 mmol), triphenylphosphine (145 mg, 0.55 mmol), 2-ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (140 mg, 0.6 mmol) and diethylazodicarboxylate (0.09 mL, 0.55 mmol) in an identical manner to Example 1 gave the title compound (120 mg).

Sources & evidence

ORD record: ord-fa94e91e47f745af9a384f68f9bd89a7
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972294B1

Reaction notes

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